Diisopropylethylamine → Ethyl 1-(2-thiopheneacetyl)-4-methyl-3-piperidinecarboxylate

HRID 432827Notes

Reaction equation

C(N1CCCC(C(OCC)=O)C1)(=O)C1C=CC=CC=1.[CH3:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH:22]1[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(N(C(C)C)CC)(C)C.[S:41]1[CH:45]=[CH:44][CH:43]=[C:42]1[CH2:46][C:47](Cl)=[O:48]>>[S:41]1[CH:45]=[CH:44][CH:43]=[C:42]1[CH2:46][C:47]([N:24]1[CH2:25][CH2:26][CH:21]([CH3:20])[CH:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23]1)=[O:48]

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 1623622-Thiopheneacetyl chloride

HCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

HCID 13658603Ethyl 4-methylpiperidine-3-carboxylate

Product 1

HCID 18760279Ethyl 1-(2-thiopheneacetyl)-4-methyl-3-piperidinecarboxylateYield 74.1%

Procedure

This reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with ethyl 4-methyl-3-piperidinecarboxylate (531.8 mg; 3.11 mmol), diisopropylethylamine (600 μl; 3.44 mmol), and thiopheneacetyl chloride (382 μl; 3.11 mmol). The crude product was purified by chromatography on silica eluting with 50% ethyl acetate/50% hexane, giving ethyl 1-(2-thiopheneacetyl)-4-methyl-3-piperidinecarboxylate (681.2 mg) as a yellow oil. MS m/z (positive ion) 397 (MH++Et3N; 70), 296 (MH+; 100).

Workup

customThe crude product was purified by chromatography on silica eluting with 50% ethyl acetate/50% hexane

Sources & evidence

ORD record: ord-a8c8525f067f4a6388e3f73df5f225c1
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664271B1

Reaction notes

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