Sodium borohydride → HCID 19095551, compound

HRID 466553Notes

Reaction equation

HRID 466553 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:26]#[N:27])[CH2:13][CH2:12][C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:16][CH2:15]3)=[CH:10][CH2:9]2)=[CH:4][CH:3]=1.C[O-].[Na+].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:26]#[N:27])[CH2:9][CH2:10][CH:11]([N:14]3[CH2:15][CH2:16][N:17]([C:20]4[N:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:18][CH2:19]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 19095576HCID 19095576, compound

Product 1

HCID 19095551HCID 19095551, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 7.3 parts of 1-(4-fluorophenyl)-4-[4-(3-pyridazinyl)-1-piperazinyl]-3-cyclohexenecarbonitrile, 1 part of sodium methoxide solution 30% and 240 parts of methanol were added portionwise 0.8 parts of sodium borohydride. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was poured onto ice water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 2-propanol, yielding 4.5 parts (61.5%) of 1-(4-fluorophenyl)-4-[4-(3-pyridazinyl)-1-piperazinyl]cyclohexanecarbonitrile; mp. 188.7° C. (compound 8).

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionthe product was extracted with trichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-9e1c12da0d2a4db59fcbbea8e66d89b2
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

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