Triethylamine → HCID 20278953, compound

HRID 1156333Notes

Reaction equation

HRID 1156333 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH2:12])=[O:11])=[O:6].Cl.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(#N)C>[NH2:12][C:10]([C:9]1[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=1[NH:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][N:30]1[CH2:31][CH2:32][CH:27]([C:25](=[O:26])[C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:24][CH:23]=2)[CH2:28][CH2:29]1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2643092-[(4-chlorobutanoyl)amino]benzamideHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 20278953HCID 20278953, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7.2 parts of 2-[(4-chloro-1-oxobutyl)amino]benzamide, 7.3 parts of (4-fluorophenyl) (4-piperidinyl)methanone hydrochloride, 10.1 parts of N,N-diethylethanamine and 120 parts of acetonitrile is stirred and refluxed for 24 hours. The reaction mixture is evaporated and water is added to the residue. The oily product is extracted with trichloromethane. The extract is dried, filtered and evaporated, yielding 10 parts (81%) of N-[2-(aminocarbonyl)phenyl]-4-(4-fluorobenzoyl)-1-piperidinebutanamide as a residue.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe reaction mixture is evaporated
  3. additionwater is added to the residue
  4. extractionThe oily product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a539135aa3f94469beec61211af5ccea
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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