Sodium Hydroxide → alpha-[3-[4-(1,2-Benzisoxazol-3-yl)-1-piperazinyl]propyl]-4-fluorobenzenemethanol

HRID 648203Notes

Reaction equation

HRID 648203 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[O:21])[CH2:13][CH2:12]2)=[N:3]1.[BH4-].[Na+].[OH-].[Na+]>C(O)C>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH:20]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[OH:21])[CH2:13][CH2:12]2)=[N:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 132324894-[4-(1,2-Benzisoxazol-3-yl)-1-piperazinyl]-1-(4-fluorophenyl)-1-butanone hydrochloride

Product 1

HCID 13232490alpha-[3-[4-(1,2-Benzisoxazol-3-yl)-1-piperazinyl]propyl]-4-fluorobenzenemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reduction of 4-[4-(1,2-benzisoxazol-3-yl)-1-piperazinyl]-1-(4-fluorophenyl)-1-butanone hydrochloride (2.0 g., 0.005 mole) with sodium borohydride (0.57 g., 0.015 mole) in 200 ml. of absolute ethanol is carried out according to the procedure of Example 13. Residual material remaining after concentration of the acidified mixture is basified with sodium hydroxide and extracted with chloroform. The combined extracts are dried over magnesium sulfate, concentrated in vacuo and triturated with ether to give 1.2 g. of the free base product. Crystallization of this material from ethanol affords analytically pure α-[3-[4-(1,2-benzisoxazol-3-yl)-1-piperazinyl]propyl]-4-fluorobenzenemethanol, m.p. 142.5°-143.5° C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe combined extracts are dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customtriturated with ether
  5. customto give 1.2 g
  6. customCrystallization of this material from ethanol

Sources & evidence

ORD record
ord-b8564a00c3614991bb41ca34ed3c82a0
Source dataset
uspto-grants-1983_10
Patent number
US04411901

Reaction notes

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