Aminoethylpiperazine → Benzyl (4,4-diethoxybutyl)carbamate

HRID 1604342Notes

Reaction equation

HRID 1604342 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-004e30bcc97e4b119b8ce29e35568eaf
Source dataset
uspto-grants-1999_11
Patent number
US05994344

Reaction notes

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