Aminoethylpiperazine → Benzyl (4,4-diethoxybutyl)carbamate

HRID 323997

Reaction equation

HRID 323997 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]([O:14][CH:15]([O:20][CH2:21][CH3:22])[CH2:16][CH2:17][CH2:18][NH2:19])[CH3:13].NCCN1CCNCC1>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:5]([O:4][C:2](=[O:3])[NH:19][CH2:18][CH2:17][CH2:16][CH:15]([O:14][CH2:12][CH3:13])[O:20][CH2:21][CH3:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8795AminoethylpiperazineHCID 10387Benzyl chloroformateHCID 806724,4-Diethoxybutylamine

Product 1

HCID 11471964Benzyl (4,4-diethoxybutyl)carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

Three portions of benzyl chloroformate (260 ml) in dichloromethane (170 ml) were added sequentially over 1 h 40 min to a vigorously stirred mixture of 4-aminobutyraldehyde diethyl acetal (910 ml) in dichloromethane (3 l ) and aqueous sodium carbonate (1M, 3 l). Stirring was continued for 50 min until gas evolution ceased. N-(2-aminoethyl)piperazine (40 ml) was added and stirring was continued for 1 h 15 min. The layers were separated and the organic layer was washed with aqueous citric acid (1M, 3.8 l) and saturated aqueous sodium bicarbonate (2 l), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a yellow oil (1.6 kg). T.l.c. (Ether) Rf 0.5.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h 15 min
  3. customThe layers were separated
  4. washthe organic layer was washed with aqueous citric acid (1M, 3.8 l) and saturated aqueous sodium bicarbonate (2 l)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-914911e2d1354ed79d63067d7130b66e
Source dataset
uspto-grants-2001_04
Patent number
US06215002B1

Linked notes

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