Thionyl Chloride → HCID 42261313, compound

HRID 432822Notes

Reaction equation

HRID 432822 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]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 743141(S)-1-benzoyl-3-piperidinecarboxylic acidHCID 15718173N-benzoylnipecotoyl chloride

Product 1

HCID 42261313HCID 42261313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Sources & evidence

ORD record
ord-7f420071fe2f4d6f8a4cda918cb08b79
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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