Sodium borohydride → HCID 19095551, compound

HRID 486449Notes

Reaction equation

HRID 486449 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-01a1e5211a574d708db46b40ddb538e6
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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