Octylamine → N-(n-octyl) 1-benzoyl-3-piperidinecarboxamide

HRID 432804Notes

Reaction equation

HRID 432804 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17]CC)=O)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCCC(C(Cl)=O)C1)(=O)C1C=CC=CC=1.[CH2:37]([NH2:45])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>>[CH2:37]([NH:45][C:15]([CH:11]1[CH2:12][CH2:13][CH2:14][N:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:10]1)=[O:17])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

4

Reactant 3

HCID 8143OctylamineHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylateHCID 15718173N-benzoylnipecotoyl chloride

Product 1

HCID 70028584N-(n-octyl) 1-benzoyl-3-piperidinecarboxamide

Procedure

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with 1-benzoyl-3-piperidinecarbonyl chloride (219.0 mg; 0.87 mmol) and commercially available octylamine (144 μl; 0.87 mmol). The crude product was purified by chromatography on silica, eluting with 100% ethyl acetate, giving N-(n-octyl) 1-benzoyl-3-piperidinecarboxamide (207.5 mg) as a colorless waxy oil. MS m/z (positive ion) 345 (MH+; 100), 216 (30).

Workup

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

Sources & evidence

ORD record
ord-cb931919c702447e9f23b944378ed6ce
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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