HCID 86746171, compound → HCID 131717567, compound

HRID 465426Notes

Reaction equation

HRID 465426 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:10][NH:11][CH:12]([CH3:28])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:16][CH:15]=2)[OH:9])[CH:5]=[CH:6][CH:7]=1>C(O)C.Cl.[Pt]=O>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:10][NH:11][CH:12]([CH3:28])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][NH:23]3)=[CH:16][CH:15]=2)[OH:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 86746171HCID 86746171, compound

Product 1

HCID 131717567HCID 131717567, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent

Procedure

3-Chloro-α-[[[2-[4-(2-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzene methanol, (2.5 g) in ethanol (40 ml) and 2M hydrochloride acid (40 ml) was hydrogenated at atmospheric pressure in the presence of platinum oxide. The reaction mixture was filtered, the filtrate neutralised with 2M sodium hydroxide solution, extracted with ethyl acetate and dried. Evaporation of the solvent gave an oil which was treated with ethereal hydrogen chloride to give 3-chloro-α-[[[2-[4-(2-piperidinylmethyloxy)phenyl]-1-methylethyl]amino]methyl] benzenemethanol, dihydrochloride m.p. 181°-198C. (methanol-ether), as a 95:5 mixture of diastereoisomers.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customEvaporation of the solvent
  5. customgave an oil which

Sources & evidence

ORD record
ord-da424cba76004a9481e56dd138f45926
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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