Sodium Hydroxide → HCID 23362149, compound

HRID 1082088Notes

Reaction equation

HRID 1082088 reaction equation
[OH-:1].[Na+].Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=O)[CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH:15]2[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:7][CH:6]=1.[BH4-].[Na+]>C(O)C.O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:1])[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH:15]2[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 67770164HCID 67770164, compound

Product 1

HCID 23362149HCID 23362149, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution containing 1.2 g (0.03 mol) of sodium hydroxide in 50 ml of an 50% by volume ethanol/water mixture, 12.41 g (0.03 mol) of 1-(4-chlorophenyl)-3-[4-hydroxy-(4-chlorophenyl)-1-piperidyl]propanone hydrochloride and then, over 1 hour 1.17 g of sodium borohydride are added. The suspension is heated at a temperature of 50° C. for 2 hours. After cooling down, the reaction mixture is filtered and washed with water to give 11.45 g of product, m.p.: 129°-132° C. After recrystallization of the latter product from 215 ml of acetonitrile, 9.1 g of title compound are obtained.

Workup

  1. temperatureAfter cooling down
  2. filtrationthe reaction mixture is filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-6f520badb0e446cbaf35cbd7717452cd
Source dataset
uspto-grants-1996_12
Patent number
US05589486

Reaction notes

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