Triethylamine → 3(-4-Acetylpiperazino)propyl 4-nitrophenyl carbonate

HRID 2085028Notes

Reaction equation

HRID 2085028 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[C:14]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]1)(=[O:16])[CH3:15].C(N(CC)CC)C>ClCCl>[C:2](=[O:3])([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[O:26][CH2:25][CH2:24][CH2:23][N:20]1[CH2:21][CH2:22][N:17]([C:14](=[O:16])[CH3:15])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 114467711-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-one

Product 1

HCID 225950113(-4-Acetylpiperazino)propyl 4-nitrophenyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl chloroformate (0.733 g; 3.63 mmol) was added to a solution of 3-(4-acetylpiperazin-1-yl)propanol [Synthesis (1997), 6, 643-648] (0.645 g; 3.46 mmol) and triethylamine (0.51 ml; 3.36 mmol) in dichloromethane (7 ml) under argon atmosphere at 0° C. The mixture was stirred at ambient temperature for 1 hour, evaporated to dryness and purified by flash chromatography, eluting with dichloromethane/ethanol (95/5) to give 3(-4-acetylpiperazino)propyl 4-nitrophenyl carbonate.

Workup

  1. customevaporated to dryness
  2. custompurified by flash chromatography
  3. washeluting with dichloromethane/ethanol (95/5)

Sources & evidence

ORD record
ord-223bd66667b242b9b35d908798cba0b6
Source dataset
uspto-grants-2004_04
Patent number
US06720323B2

Reaction notes

Loading…