Triethylamine → tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylate

HRID 1937823Notes

Reaction equation

HRID 1937823 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([N:16](CC)CC)[CH3:15].ClCCN>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:14][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133692-ChloroethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 1514400tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-tert-butoxycarbonyl-piperazin (5 g, 26.8 mmol), triethylamine (7.44 ml, 53.6 mmol), and chloroethylamine (3.11 g, 26.8 mmol) in dimethylformamide (50 ml) was stirred at room temperature for 72 hours. The reaction mixture was filtered, partitioned between H2O and ethyl acetate. The aqueous phase was lyophilized, the residue stirred with methanol and the precipitate collected by suction. The precipitate was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia=9/1/0.1) to give 1.6 g (26%) of the desired product. MS m/z: 230 ((M+H)+, 91%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompartitioned between H2O and ethyl acetate
  3. customthe precipitate collected by suction
  4. customThe precipitate was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia=9/1/0.1)

Sources & evidence

ORD record
ord-f2c53517cb274bed9c83e7220f84e317
Source dataset
uspto-grants-2002_05
Patent number
US06395737B1

Reaction notes

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