Triethylamine → HCID 13825066, compound

HRID 648501Notes

Reaction equation

HRID 648501 reaction equation
Cl.[F:2][C:3]([F:25])([F:24])[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15]3[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=3)=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1.Cl.[F:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[O:35])=[CH:30][CH:29]=1.C(N(CC)CC)C>C(Cl)Cl>[F:27][C:28]1[CH:29]=[CH:30][C:31]([S:34]([CH:36]2[CH2:41][CH2:40][N:39]([C:19](=[O:20])[C:18]3[CH:22]=[CH:23][C:15]([NH:14][C:8]4[C:7]5[C:12](=[CH:13][C:4]([C:3]([F:25])([F:24])[F:2])=[CH:5][CH:6]=5)[N:11]=[CH:10][CH:9]=4)=[CH:16][CH:17]=3)[CH2:38][CH2:37]2)=[O:35])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13603946HCID 13603946, compoundHCID 13825047HCID 13825047, compound

Product 1

HCID 13825066HCID 13825066, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[[7-(Trifluoromethyl)-4-quinolyl]amino]benzoyl chloride hydrochloride (14.7 g) was added slowly to a stirred mixture of 4-[(4-fluorophenyl)sulfinyl]piperidine hydrochloride (10.0 g) and triethylamine (26.4 ml) in dry methylene chloride (440 ml) at room temperature. The resultant mixture was stirred at the same temperature for 3 hours, and concentrated to dryness in vacuo. Water was added to the residue and the precipitated powder was collected by filtration, washed with water, and dried to give a powder. The powder was washed with methylene chloride to give 4-[(4-fluorophenyl)sulfinyl]-1-[4-[[7-(trifluoromethyl)-4-quinolyl]amino]benzoyl]piperidine (13.60 g) as colourless powder.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. additionWater was added to the residue
  3. filtrationthe precipitated powder was collected by filtration
  4. washwashed with water
  5. customdried
  6. customto give a powder
  7. washThe powder was washed with methylene chloride

Sources & evidence

ORD record
ord-4bab41e2517a44f882bf36be8d256cea
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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