Ethyl nipecotate → Ethyl 1-(2-thiophen-2-ylacetyl)piperidine-3-carboxylate

HRID 432795Notes

Reaction equation

HRID 432795 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]1C=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCC(C(OCC)=O)C1.[S:31]1C=CC=C1CC(Cl)=O>>[S:31]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:2][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]

Participants

4

Reactant 3

HCID 98969Ethyl nipecotateHCID 1623622-Thiopheneacetyl chlorideHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

Product 1

HCID 3273150Ethyl 1-(2-thiophen-2-ylacetyl)piperidine-3-carboxylate

Procedure

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with ethyl nipecotate (201.8 mg; 1.28 mmol) and commercially available 2-thiopheneacetyl chloride (158 μl; 1.28 mmol). The crude product was distilled at 225° C./0.1 torr, giving ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxylate (250.5 mg) as a yellow oil, which solidified on standing. MS m/z (positive ion) 304 (M+Na+; 60), 282 (MH+; 100).

Workup

  1. distillationThe crude product was distilled at 225° C./0.1 torr

Sources & evidence

ORD record
ord-36858d19e2e44aedb4807dac805139e2
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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