Hydrochloric Acid → HCID 14674162, compound

HRID 1614209Notes

Reaction equation

HRID 1614209 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:15][CH3:16])=[O:4].[ClH:17].[F:18][C:19]1[CH:32]=[CH:31][C:22]([C:23]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1.C(N(CC)CC)C.Cl>C(O)C>[ClH:17].[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([CH:25]2[CH2:30][CH2:29][N:28]([CH2:2][C:3]([C:5]3[CH:14]=[CH:13][C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:6]=3[O:15][CH3:16])=[O:4])[CH2:27][CH2:26]2)=[O:24])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 12698899HCID 12698899, compound

Product 1

HCID 14674162HCID 14674162, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.5 g of 2-bromo-1'-methoxy-2'-acetonaphthone, 1.3 g of 4-(p-fluorobenzoyl)piperidine hydrochloride, and 1.6 g of triethylamine were added to 60 ml of ethanol. The mixture was refluxed for 15 min. The solvent was distilled off, and dichloromethane was added to the residue. The mixture was washed with water and dried. The dichloromethane was distilled off, and the residue was purified by column chromatography (silica gel) to prepare an oleaginous intended compound. The compound was converted into a hydrochloride by an ordinary method and then recrystallized to prepare 1.38 g of an intended hydrochloride.

Workup

  1. temperatureThe mixture was refluxed for 15 min
  2. distillationThe solvent was distilled off
  3. additiondichloromethane was added to the residue
  4. washThe mixture was washed with water
  5. customdried
  6. distillationThe dichloromethane was distilled off
  7. customthe residue was purified by column chromatography (silica gel)
  8. customto prepare an oleaginous intended compound
  9. customrecrystallized
  10. customto prepare 1.38 g of an intended hydrochloride

Sources & evidence

ORD record
ord-314732657de543559eb902e08595b3cc
Source dataset
uspto-grants-1993_03
Patent number
US05196439

Reaction notes

Loading…