Hydrochloric Acid → alpha-[3-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]propyl]-4-fluorobenzenemethanol

HRID 648201Notes

Reaction equation

HRID 648201 reaction equation
[BH4-].[Na+].Cl.[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[O:23])[CH2:15][CH2:14]2)=[N:5]1.Cl>C(O)C>[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH:22]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[OH:23])[CH2:15][CH2:14]2)=[N:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 132324854-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]-1-(4-fluorophenyl)-1-butanone hydrochloride

Product 1

HCID 13232486alpha-[3-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]propyl]-4-fluorobenzenemethanolYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.0 g., 0.026 mole) is added portionwise to a stirred suspension of 4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]-1-(4-fluorophenyl)-1-butanone hydrochloride (3.34 g., 0.008 mole) in 150 ml. of absolute ethanol. The mixture is stirred for a 20 hr. period, acidified with ethanolic hydrogen chloride, stirred for an additional 2 hr. period and concentrated in vacuo. Residual material is partitioned between chloroform and 1 N aqueous sodium hydroxide and the chloroform phase dried over magnesium sulfate and concentrated in vacuo to afford 2.31 g. (69% yield) of the title compound as the free base. The free base is converted to the hydrochloride in ethanol with ethanolic hydrogen chloride to afford α-[3-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]propyl]-4-fluorobenzenemethanol hydrochloride, m.p. 200°-202° C.

Workup

  1. stirringstirred for an additional 2 hr
  2. concentrationperiod and concentrated in vacuo
  3. customResidual material is partitioned between chloroform and 1 N aqueous sodium hydroxide
  4. dry with materialthe chloroform phase dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford 2.31 g

Sources & evidence

ORD record
ord-16c2b16b70b543ff9073036fcd7ce666
Source dataset
uspto-grants-1983_10
Patent number
US04411901

Reaction notes

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