3-Hydroxypiperidine → 1-(2-Thiopheneacetyl)-3-hydroxypiperidine

HRID 432819Notes

Reaction equation

C(N1CCCC(C(OCC)=O)C1)(=O)C1C=CC=CC=1.[OH:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][C:33](Cl)=[O:34].C(N(C(C)C)CC)(C)C>>[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][C:33]([N:23]1[CH2:24][CH2:25][CH2:26][CH:21]([OH:20])[CH2:22]1)=[O:34]

Participants

Reactant 4

HCID 232933-Hydroxypiperidine

HCID 81531Diisopropylethylamine

HCID 1623622-Thiopheneacetyl chloride

HCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

Product 1

HCID 187602651-(2-Thiopheneacetyl)-3-hydroxypiperidineYield 66.1%

Procedure

This reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with commercially available 3-hydroxypiperidine (1.03 g; 10.2 mmol) and 2-thiopheneacetyl chloride (1.2 ml; 10 mmol) and diisopropylethylamine (1.9 ml; 10.9 mmol). The crude product was purified by chromatography on silica, eluting with 100% ethyl acetate, giving 1-(2-thiopheneacetyl)-3-hydroxypiperidine (1.49 g) as a yellow oil, which solidified on standing. MS m/z (positive ion) 248 (M+Na+; 50), 226 (MH+; 100).

Workup

customThe crude product was purified by chromatography on silica
washeluting with 100% ethyl acetate

Sources & evidence

ORD record: ord-e7dd3b5d16804143ab01cc7939349073
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664271B1

Reaction notes

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