Sodium borohydride → HCID 12834396, compound

HRID 1065275Notes

Reaction equation

HRID 1065275 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:30]#[N:31])[CH2:13][CH2:12][C:11]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[NH:22][C:21]4=[O:29])[CH2:16][CH2:15]3)=[CH:10][CH2:9]2)=[CH:4][CH:3]=1.C[O-].[Na+].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:30]#[N:31])[CH2:13][CH2:12][CH:11]([N:14]3[CH2:15][CH2:16][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[NH:22][C:21]4=[O:29])[CH2:18][CH2:19]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 20540241HCID 20540241, compound

Product 1

HCID 12834396HCID 12834396, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 11 parts of 1-(4-chlorophenyl)-4-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-3-cyclohexene-1-carbonitrile, 5 parts of sodium methoxide solution 30% and 320 parts of methanol are added portionwise 3 parts of sodium borohydride. Upon completion, stirring is continued first for one hour at reflux temperature and further overnight at room temperature. The reaction mixture is poured onto water. The precipitated product is filtered off and boiled in methanol. The product is filtered off and dried, yielding 5.3 parts of 1-(4-chlorophenyl)-4-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]cyclohexanecarbonitrile; mp. 299° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. filtrationThe precipitated product is filtered off
  3. filtrationThe product is filtered off
  4. customdried

Sources & evidence

ORD record
ord-5f19f8978de44c80a9b7765800ce6d6a
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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