Ethylamine hydrochloride → N-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxamide

HRID 432806Notes

Reaction equation

HRID 432806 reaction equation
[C:1]([N:9]1CCCC(C(OCC)=O)C1)(=O)[C:2]1C=CC=CC=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][CH2:31][CH:30]([C:34](Cl)=[O:35])[CH2:29]1)=[O:27].C(N(C(C)C)CC)(C)C.Cl.C(N)C>>[CH2:1]([NH:9][C:34]([CH:30]1[CH2:31][CH2:32][CH2:33][N:28]([C:26](=[O:27])[CH2:25][C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)[CH2:29]1)=[O:35])[CH3:2]

Participants

5

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylateHCID 187602711-(2-Thiopheneacetyl)-3-piperidinecarbonyl chloride

Product 1

HCID 18760269N-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxamide

Procedure

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with 1-(2-thiopheneacetyl)-3-piperidinecarbonyl chloride (609.8 mg; 2.25 mmol), diisopropylethylamine (920 μl; 5.28 mmol) and commercially available ethylamine hydochloride (204.8 mg; 2.51 mmol). The crude product was purified by chromatography on silica, eluting with 100% ethyl acetate, giving N-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxamide (437.5 mg) as a thick, brown syrup. MS m/z (positive ion) 303 (M+Na+; 25), 281 (MH+; 100), 157 (25).

Workup

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

Sources & evidence

ORD record
ord-b409377c7f284d1fbd775f56a56ef64b
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

Loading…