Diethylamine → benzyl 4-(N,N-diethylamino)butanoate

HRID 266127Notes

Reaction equation

HRID 266127 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[CH2:15]([NH:17][CH2:18][CH3:19])[CH3:16]>ClCCl>[CH2:15]([N:17]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])[CH2:18][CH3:19])[CH3:16]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 3832489Benzyl 4-bromobutanoate

Product 1

HCID 19032368benzyl 4-(N,N-diethylamino)butanoateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of benzyl 4-bromobutanoate (58.6 diethylamine (58.3 g) and dichloromethane (1000 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate gave benzyl 4-(N,N-diethylamino)butanoate (33.8 g, 60%).

Workup

  1. temperatureunder reflux for 14 hours
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe fractions eluted with ethyl acetate

Sources & evidence

ORD record
ord-5a0cea2b15534838b31d8da8b7eb66e2
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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