Hydrochloric Acid → HCID 15463122, compound

HRID 613255Notes

Reaction equation

HRID 613255 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:14]1[CH:26]=[CH:25][C:17]([C:18]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[O:19]=[C:18]([C:17]1[CH:25]=[CH:26][C:14]([N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)=[CH:15][CH:16]=1)[CH2:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 1013593-(4-Fluorobenzoyl)propionic acid

Product 1

HCID 15463122HCID 15463122, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A stirred mixture of 4-phenyl-piperidine (10.4 g, 0.064 mol), 3-(4-fluorobenzoyl)-propionic acid (12.1 g, 0.062 mol), and potassium carbonate (17.5 g, 0.13 mol) in DMSO (15 mL) was heated under an atmosphere of nitrogen at 120° C. for 18 hours. The mixture was allowed to cool, diluted with water (100 mL), and brought to pH 2 dropwise with 1 M HCl. The resulting solid was filtered, washed with water, and dried in vacuo to yield a pale orange solid as the title compound (11.2 g, %C,H,N found: 74.54, 6.98, 4.07).

Workup

  1. temperatureto cool
  2. filtrationThe resulting solid was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f4604844ba35491cbd049841311836ec
Source dataset
uspto-grants-1999_12
Patent number
US06008220

Reaction notes

Loading…