Dimethyl Sulfoxide → 1-[(3,4-Dichlorophenyl)acetyl]-4-(phenylmethyl)-2-piperazine carboxaldehyde
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH2:19][C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH:23]2[CH2:35][OH:36])=[O:21])[CH:15]=[CH:16][C:17]=1[Cl:18].C(N(CC)CC)C>ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]([CH2:19][C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:24][CH:23]2[CH:35]=[O:36])=[O:21])[CH:15]=[CH:16][C:17]=1[Cl:18]Participants
6
Procedure
A solution of dimethylsulphoxide (369 mg) in dry dichloromethane (3 ml) was added to a stirred solution of oxalyl chloride (300 mg) in dry dichloromethane (7 ml) at -60° under nitrogen and the resulting solution was stirred at -60° to -64° for 30 minutes. The product of stage (i) (774 mg) in dry dichloromethane (5 ml) was added dropwise and the reaction mixture was stirred between -60° to -63° for 2.5 h. Triethylamine (995 mg) was added and the mixture was allowed to warm to -20°, and quenched with water (15 ml). The layers were separated and the aqueous phase was further extracted with dichloromethane (2×15 ml). The combined organic extracts were dried and evaporated to give the title compound as an oil (830 mg).
Workup
- stirringthe reaction mixture was stirred between -60° to -63° for 2.5 h
- temperatureto warm to -20°
- customquenched with water (15 ml)
- customThe layers were separated
- extractionthe aqueous phase was further extracted with dichloromethane (2×15 ml)
- customThe combined organic extracts were dried
- customevaporated
Sources & evidence
- ORD record
- ord-8021e28909754f6dad4827ee71621126
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05116842
Reaction notes
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