Benzyl chloroformate → Benzyl ethyl piperidine-1,3-dicarboxylate

HRID 432791Notes

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])C1C=CC=CC=1.N1CCCC(C(OCC)=O)C1.ClC([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=O>>[CH2:35]([O:34][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:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Reactant 3

HCID 10387Benzyl chloroformate

HCID 98969Ethyl nipecotate

HCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

Product 1

HCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylate

Procedure

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with ethyl nipecotate (209.9 mg; 1.33 mmol and benzyl chloroformate (190 μl; 1.33 mmol). The crude product was distilled at 220° C./0.1 torr, giving ethyl 1-benzyloxycarbonyl-3-piperidinecarboxylate (236.5 mg) as a colorless oil. MS m/Z (positive ion) 539 ([dimer-OEt]+; 50), 337 (M+2Na+; 25), 314 (M+Na+; 50), 292 (MH+; 100), 247.5 (M-OEt; 90), 158 (50).

Workup

distillationThe crude product was distilled at 220° C./0.1 torr

Sources & evidence

ORD record: ord-05481e83f1b34492a5c9a7a84d1586d0
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664271B1

Reaction notes

Loading…