Sulfate Ion → 1-(2-Cyclohexyl-4-quinolyl)-3-(4-piperidyl)-1-propanol

HRID 65222

Reaction equation

HRID 65222 reaction equation
Cl.[CH:2]1([C:8]2[CH:17]=[C:16]([C:18](=[O:27])[CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].C[O-].[Na+].[BH4-].[Na+].S([O-])([O-])(=O)=O>C(O)C>[CH:2]1([C:8]2[CH:17]=[C:16]([CH:18]([OH:27])[CH2:19][CH2:20][CH:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

7

Reactant 5

HCID 1117Sulfate IonHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 202341271-(2-Cyclohexyl-4-quinolyl)-3-(4-piperidyl)-1-propanone monohydrochloride

Product 1

HCID 202341161-(2-Cyclohexyl-4-quinolyl)-3-(4-piperidyl)-1-propanolYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The operation was as in Example 5, starting from 5.1 g of 1-(2-cyclohexyl-4-quinolyl)-3-(4-piperidyl)-1-propanone monohydrochloride, 1.3 ml of a 10N aqueous solution of sodium hydroxide (instead of sodium methylate) and 0.53 g of sodium borohydride in 100 ml of ethanol. 1.3 g of 1-(2-cyclohexyl-4-quinolyl)-3-(4-piperidyl)-1-propanol (racemic) were finally obtained in the form of the sulfate melting at 260° C.

Sources & evidence

ORD record
ord-e12560ad974f41aba543abacd5ee998d
Source dataset
uspto-grants-1986_09
Patent number
US04613607

Linked notes

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