|
General Description |
1-Boc-piperazine is an N-Boc protected piperazine. Crosscoupling of 1-Boc-piperazine with aryl iodides using CuBr/1,1′-bi-2-naphthol (catalyst) and K3PO4 (base) has been reported. 1-Boc-piperazine undergoes Buchwald-Hartwig coupling reactions with aryl halides. 1-Boc-piperazine can be prepared in 80% yield via solvent-free N-Boc protection catalyzed by iodine. |
InChI:InChI=1/C9H18N2O2/c1-9(2,3)13-8(12)11-6-4-10-5-7-11/h10H,4-7H2,1-3H3/p+1
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piperazine
di-tert-butyl dicarbonate
1-t-Butoxycarbonylpiperazine
| Conditions | Yield |
|---|---|
|
piperazine;
With
2-chlorotrityl resin; N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 20 ℃;
for 12h;
di-tert-butyl dicarbonate;
With
triethylamine;
In
dichloromethane;
at 20 ℃;
for 4h;
With
trifluoroacetic acid;
In
dichloromethane;
|
98% |
|
With
1-methylimidazolium tetrafluoroborate;
at 30 - 35 ℃;
for 0.0333333h;
|
98% |
|
With
formic acid; acetamidine hydrochloride;
In
methanol; water;
at 20 ℃;
for 2h;
Reagent/catalyst;
Solvent;
|
98.6% |
|
piperazine; di-tert-butyl dicarbonate;
In
isopropyl alcohol;
at 20 ℃;
for 4h;
With
succinic acid;
In
isopropyl alcohol;
for 2h;
|
97% |
|
With
nano-sphere silica sulfuric acid;
In
neat (no solvent);
at 20 ℃;
for 0.0833333h;
chemoselective reaction;
|
96% |
|
In
dichloromethane;
at 0 ℃;
Inert atmosphere;
|
96% |
|
With
sulfonic-acid-functionalized silica;
In
dichloromethane;
at 20 ℃;
for 0.166667h;
|
94% |
|
In
methanol;
for 2.5h;
|
94% |
|
piperazine;
In
methanol;
at 20 ℃;
for 0.333333h;
di-tert-butyl dicarbonate;
In
methanol;
at 10 ℃;
for 5h;
|
93.7% |
|
With
triethylamine;
In
methanol;
at 20 ℃;
for 4h;
|
92.5% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 0.5h;
|
92% |
|
With
sulfonated reduced graphene oxide;
In
neat (no solvent);
at 20 ℃;
for 0.25h;
|
92% |
|
piperazine;
With
sulfuric acid;
In
water;
at 0 - 5 ℃;
for 0.5h;
di-tert-butyl dicarbonate;
In
water;
at 0 - 5 ℃;
for 1h;
|
90% |
|
With
triethylamine;
In
dichloromethane;
at 0 - 20 ℃;
|
90% |
|
In
methanol;
at 0 - 20 ℃;
for 16h;
|
90% |
|
In
neat (no solvent);
at 100 ℃;
for 0.0333333h;
chemoselective reaction;
Microwave irradiation;
Green chemistry;
|
88% |
|
With
acetic acid;
In
methanol; water;
at 0 - 20 ℃;
|
87% |
|
With
sodium hydroxide;
In
water; tert-butyl alcohol;
at 0 - 20 ℃;
|
86.5% |
|
In
methanol;
at 100 ℃;
for 0.0333333h;
Microwave irradiation;
Inert atmosphere;
|
86% |
|
With
triethylamine;
In
methanol;
at 20 ℃;
|
86% |
|
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 27 ℃;
for 20h;
|
85% |
|
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 20 ℃;
for 3h;
|
85% |
|
With
sodium hydroxide;
In
water; tert-butyl alcohol;
at 20 ℃;
for 1.5h;
Inert atmosphere;
|
84% |
|
With
triethylamine;
In
methanol;
at 20 ℃;
|
84% |
|
In
1,4-dioxane;
for 26.5h;
|
83% |
|
In
dichloromethane;
|
83% |
|
In
dichloromethane;
for 22h;
|
83% |
|
In
dichloromethane;
at 20 ℃;
for 25h;
|
81% |
|
With
iodine;
at 20 ℃;
for 0.5h;
|
80% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 26h;
|
78% |
|
In
dichloromethane;
at 0 - 25 ℃;
for 3h;
|
76% |
|
In
dichloromethane;
at 20 ℃;
|
75% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 24h;
|
75% |
|
In
dichloromethane;
at 0 - 20 ℃;
|
74% |
|
With
sodium hydroxide;
In
water; tert-butyl alcohol;
at 20 ℃;
for 12h;
|
74% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 13h;
Inert atmosphere;
|
73% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 16h;
Inert atmosphere;
Schlenk technique;
|
73% |
|
In
dichloromethane;
for 24h;
|
72% |
|
piperazine; di-tert-butyl dicarbonate;
In
methanol;
at 0 - 20 ℃;
With
citric acid;
In
diethyl ether; water;
Extraction;
With
potassium carbonate;
In
water;
pH=11;
|
71% |
|
With
sodium hydroxide;
In
water; isopropyl alcohol;
at 20 ℃;
for 18h;
|
70% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 5h;
|
68% |
|
In
dichloromethane;
at 20 ℃;
Inert atmosphere;
|
67% |
|
In
methanol;
at 0 - 20 ℃;
for 36h;
|
66% |
|
In
dichloromethane;
at 20 ℃;
|
66% |
|
In
dichloromethane;
at 0 ℃;
for 1.33333h;
|
65.2% |
|
In
dichloromethane;
at 0 ℃;
for 1.33333h;
|
65.2% |
|
In
dichloromethane;
at 20 ℃;
Cooling with ice;
Inert atmosphere;
|
63% |
|
In
dichloromethane;
at 0 - 20 ℃;
|
61% |
|
With
hydrogenchloride;
In
acetone;
for 1h;
Ambient temperature;
|
58% |
|
In
dichloromethane;
at 0 - 20 ℃;
|
57% |
|
With
sodium hydroxide;
In
water; isopropyl alcohol;
at 20 ℃;
for 18h;
|
57% |
|
In
dichloromethane;
at 20 ℃;
for 21h;
|
56% |
|
In
methanol;
at 0 - 50 ℃;
|
55% |
|
In
dichloromethane;
at 20 ℃;
|
54% |
|
In
methanol;
at 50 ℃;
for 1h;
|
50% |
|
In
dichloromethane;
at 0 ℃;
|
50% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 24h;
|
50% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 24h;
|
50% |
|
In
dichloromethane;
at 20 ℃;
|
50% |
|
With
potassium carbonate; toluene-4-sulfonic acid hydrazide;
In
dichloromethane;
at 20 ℃;
|
50% |
|
In
dichloromethane;
at 0 ℃;
for 24h;
|
50% |
|
With
silica-based strong cation exchanger;
In
methanol;
|
49% |
|
With
acetic acid;
at 20 ℃;
for 2h;
Inert atmosphere;
|
46% |
|
In
dichloromethane;
at 0 ℃;
for 1h;
Time;
|
44% |
|
In
dichloromethane;
at 20 ℃;
|
43.9% |
|
In
dichloromethane;
at 0 - 20 ℃;
|
39% |
|
In
dichloromethane;
for 2h;
Cooling with ice;
|
37% |
|
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 20 ℃;
for 24h;
Inert atmosphere;
|
37% |
|
In
dichloromethane;
at 0 - 20 ℃;
for 5h;
|
33% |
|
piperazine;
With
sodium hydroxide;
In
water; tert-butyl alcohol;
at 0 ℃;
Inert atmosphere;
Schlenk technique;
di-tert-butyl dicarbonate;
In
tetrahydrofuran; light petroleum;
at 0 - 20 ℃;
for 18h;
Inert atmosphere;
Schlenk technique;
|
33% |
|
In
dichloromethane;
at 0 ℃;
for 1h;
|
30% |
|
In
methanol;
at 0 - 20 ℃;
for 48h;
|
|
|
In
isopropyl alcohol;
at 20 ℃;
for 0.5h;
|
|
|
With
TEA;
In
dichloromethane;
at 0 - 20 ℃;
|
|
|
In
methanol;
at -78 - 20 ℃;
for 1h;
|
|
|
In
N-ethyl-N,N-diisopropylamine; acetonitrile;
|
66.32 g (79%) |
|
With
sodium hydroxide;
In
water; tert-butyl alcohol;
|
|
|
In
dichloromethane;
|
|
|
In
dichloromethane;
at 0 ℃;
for 2h;
|
|
|
In
methanol;
at 0 - 20 ℃;
for 48.5h;
Inert atmosphere;
|
|
|
In
dichloromethane;
at 0 ℃;
|
|
|
In
dichloromethane;
|
|
|
With
triethylamine;
In
chloroform;
at 0 - 5 ℃;
for 4h;
|
|
|
With
sodium carbonate;
In
dichloromethane;
at 20 ℃;
|
|
|
In
methanol;
at 20 ℃;
for 18h;
|
|
|
In
dichloromethane;
at 20 ℃;
|
|
|
In
dichloromethane;
at 0 - 20 ℃;
|
|
|
piperazine;
With
acetic acid;
at 0 - 20 ℃;
for 0.666667h;
Inert atmosphere;
di-tert-butyl dicarbonate;
With
acetic acid;
at 0 - 20 ℃;
for 2.5h;
|
|
|
With
triethylamine;
In
acetonitrile;
at 20 ℃;
for 4h;
|
|
|
In
water; acetic acid;
at 0 - 20 ℃;
|
|
|
With
sodium hydroxide;
In
1,4-dioxane; water;
at 0 - 20 ℃;
for 12h;
|
|
|
In
methanol;
at 25 - 30 ℃;
for 0.5h;
|
|
|
With
sodium hydrogencarbonate;
In
methanol;
at 0 - 20 ℃;
|
|
|
In
dichloromethane;
at 0 - 20 ℃;
for 24h;
|
2-oxo-4-morpholinecarboxylic acidtert-butyl ester
1-t-Butoxycarbonylpiperazine
| Conditions | Yield |
|---|---|
|
With
ammonia;
In
methanol;
at 40 ℃;
for 2.5h;
under 1500.15 Torr;
Solvent;
Inert atmosphere;
Autoclave;
|
91.8% |
piperazine
N-(tert-butyloxycarbonyl) azide
di-tert-butyl dicarbonate
1-(tert-butyl) 4-methyl piperazine-1,4-dicarboxylate
4-(4-carboxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester
tert-Butyl 4-(p-Vinylbenzyl)piperazine-1-carboxylate
4-[3-(2-Benzoyloxy-ethyl)-imidazo[1,2-a]pyrazin-8-yl]-piperazine-1-carboxylic acid tert-butyl ester
tert-butyl 4-(p-isopropylbenzyl)piperazine-1-carboxylate
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