Thionyl Chloride → (S)-1-benzoyl-3-piperidinecarbonyl chloride
Reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([Cl:17])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCC[C@H](C(O)=O)C1)(=O)C1C=CC=CC=1.S(Cl)(Cl)=O>ClCCl>[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([Cl:17])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Procedure
The reaction was run in the same manner as 1-benzoyl-3-piperidinecarbonyl chloride, starting with (S)-1-benzoyl-3-piperidinecarboxylic acid (6.30 g; 27.0 mmols), thionyl chloride (16.06 g, 135 mmol), and dry dichloromethane (150 ml), giving (S)-1-benzoyl-3-piperidinecarbonyl chloride as a light yellow oil, which was used without further purification. MS (in CH3CN) m/z (positive ion) 503 (40), 485 (42), 467 (40), 254 (60), 252 (MH+; 100), 234 (68).