Benzoyl chloride → (S)-ethyl 1-benzoyl-3-piperidinecarboxylate

HRID 432801

Reaction equation

HRID 432801 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCC[C@H](C(OCC)=O)C1.C(Cl)(=O)C1C=CC=CC=1>>[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 187784Ethyl (3S)-piperidine-3-carboxylateHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

Product 1

HCID 670251(S)-ethyl 1-benzoyl-3-piperidinecarboxylate

Procedure

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with commercially available (S)-ethyl nipecotate (203 mg; 1.29 mmol; Chemi SpA; Italy) and benzoyl chloride (150 μl; 1.29 mmol). The crude product was distilled at 200° C./0.1 torr, giving (S)-ethyl 1-benzoyl-3-piperidinecarboxylate (171.7 mg) as a colorless oil. MS m/z (positive ion) 545 (dimer+Na+; 15), 523 (dimer+; 10), 284 (M+Na+; 25), 262 (MH+; 100).

Workup

  1. distillationThe crude product was distilled at 200° C./0.1 torr

Sources & evidence

ORD record
ord-52557d95f02e4990bcaf292be7e47464
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Linked notes

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