Hydrochloric Acid → HCID 131717837, compound

HRID 1614604Notes

Reaction equation

HRID 1614604 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=[N:9][OH:10])=[CH:4][CH:3]=1.[ClH:27]>C(O)C.[Ni].CO>[OH2:10].[ClH:27].[ClH:27].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:15][CH2:16]2)[NH2:9])=[CH:6][CH:7]=1.[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:15][CH2:16]2)[NH2:9])=[CH:6][CH:7]=1.[ClH:27].[ClH:27]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 73653364HCID 73653364, compound

Product 1

HCID 131717837HCID 131717837, compoundYield 54.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A suspension of the (4-fluorophenyl)[1-(3-phenoxypropyl)-4-piperidinyl]methanone oxime (5.00 g, 0.014 mol) in 100 mL of ethanol was subjected to hydrogenation (52 psi) in the presence of Raney nickel for 16 hours at room temperature. The catalyst was removed by filtration, and ethanol was removed by the rotary evaporator to give a clear oil. This oil was converted to the HCl salt in methanol using ethereal HCl. A white solid was isolated and dried in vacuo 16 hours at 80° C. in the presence of phosphorus pentoxide. This process provided 3.22 g (54.2%) of white crystalline solid, mp 247°-248° C. (dec).

Workup

  1. customThe catalyst was removed by filtration, and ethanol
  2. customwas removed by the rotary evaporator
  3. customto give a clear oil
  4. customA white solid was isolated
  5. dry with materialdried in vacuo 16 hours at 80° C. in the presence of phosphorus pentoxide

Sources & evidence

ORD record
ord-3d92debeea4e43ec8a3d80fd370166a6
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

Loading…