Triethylamine → HCID 19429448, compound
Reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH2:16])[CH3:15])=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][C:4]([NH:16][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1)[CH3:15])=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-chloropropionyl chloride (32.7 g) in methylene chloride (40 ml) was added dropwise to stirred solution of (±) 1-(4-chlorophenyl)ethylamine (40 g) in dichloromethane (260 ml) with triethylamine (28.4 g) over 45 minutes at 0°-5° C. The temperature was allowed to rise to 25° C. and the mixture stirred for a further 2 hours. The cooled reaction mixture was washed with saturated aqueous sodium bicarbonate (260 ml). The organic layer was separated, dried and filtered and the filtrate evaporated. The residue was triturated with petrol, collected by filtration and recrystallised from ethyl acetate to give 3-chloro-N-[1-(4-chlorophenyl)ethyl]propionamide, m.p. 86°-91° C. This product was obtained as a mixture with N-[1-(4-chlorophenyl)ethyl]acrylamide but was sufficiently pure for synthetic purposes. The acrylamide does not react and was removed on work-up in the next stage.
Workup
- customto rise to 25° C.
- customThe cooled reaction mixture
- washwas washed with saturated aqueous sodium bicarbonate (260 ml)
- customThe organic layer was separated
- customdried
- filtrationfiltered
- customthe filtrate evaporated
- customThe residue was triturated with petrol
- filtrationcollected by filtration
- customrecrystallised from ethyl acetate
Sources & evidence
- ORD record
- ord-a544415754b6478f97b2cee8616719f0
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05547972
Reaction notes
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