Sodium borohydride → 1-[2-(1,1-Dimethyl-ethyl)-4-quinolyl]-3-[1-(2-phenyl-ethyl)-4-piperidyl]-1-propanol dihydrochloride

HRID 65219Notes

Reaction equation

HRID 65219 reaction equation
[ClH:1].Cl.[CH3:3][C:4]([C:7]1[CH:16]=[C:15]([C:17](=[O:34])[CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22][CH2:21]2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)([CH3:6])[CH3:5].C[O-].[Na+].[BH4-].[Na+]>CO>[ClH:1].[ClH:1].[CH3:6][C:4]([C:7]1[CH:16]=[C:15]([CH:17]([OH:34])[CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22][CH2:21]2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)([CH3:3])[CH3:5]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 202341291-[2-(1,1-Dimethyl-ethyl)-4-quinolyl]-3-[1-(2-phenyl-ethyl)-4-piperidyl]-1-propanone dihydrochloride

Product 1

HCID 202341241-[2-(1,1-Dimethyl-ethyl)-4-quinolyl]-3-[1-(2-phenyl-ethyl)-4-piperidyl]-1-propanol dihydrochlorideYield 167.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The operation was as in Example 5, starting from 10 g of 1-[2-(1,1-dimethyl-ethyl)-4-quinolyl]-3-[1-(2-phenyl-ethyl)-4-piperidyl]-1-propanone dihydrochloride, 2.2 g of sodium methylate and 0.8 g of sodium borohydride in 250 ml of methanol. 8.4 g of 1-[2-(1,1-dimethyl-ethyl)-4-quinolyl]-3-[1-(2-phenyl-ethyl)-4-piperidyl]-1-propanol dihydrochloride (racemic), which melted at 190° C. were obtained.

Sources & evidence

ORD record
ord-cd969a6e26d34252a9635315ae82f8ec
Source dataset
uspto-grants-1986_09
Patent number
US04613607

Reaction notes

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