2-Thiophenecarbonyl chloride → Ethyl 1-(2-thienylcarbonyl)-3-piperidinecarboxylate

HRID 432794Notes

Reaction equation

HRID 432794 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=C[CH:5]=[CH:4][CH:3]=1.N1CCCC(C(OCC)=O)C1.[S:31]1C=CC=C1C(Cl)=O>>[S:31]1[CH:5]=[CH:4][CH:3]=[C:2]1[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 789282-Thiophenecarbonyl chlorideHCID 98969Ethyl nipecotateHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

Product 1

HCID 2904303Ethyl 1-(2-thienylcarbonyl)-3-piperidinecarboxylate

Procedure

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with ethyl nipecotate (202.9 mg; 1.29 mmol) and commercially available 2-thiophenecarbonyl chloride (138 μl; 1.29 mmol). The crude product was distilled at 225° C./0.1 torr, giving ethyl (2-thiophenecarbonyl)-3-piperidinecarboxylate (249.8 mg) as a yellow oil. MS m/z (positive ion) 290 (M+Na+; 40), 268 (MH+; 100).

Workup

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

Sources & evidence

ORD record
ord-af32ce0ff436400f9149418448792eb6
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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