Sodium borohydride → N-(5-(pyrrolidin-1-yl)-2-(3,4,5-trimethoxybenzylamino)phenyl)benzamide

HRID 1888955Notes

Reaction equation

HRID 1888955 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][C:9](/[N:21]=[CH:22]/[C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)=[C:10]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH:21][CH2:22][C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)=[C:10]([NH:12][C:13](=[O:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178492117HCID 178492117, compound

Product 1

HCID 68516839N-(5-(pyrrolidin-1-yl)-2-(3,4,5-trimethoxybenzylamino)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of compound (E)-N-(5-(pyrrolidin-1-yl)-2-(3,4,5-trimethoxybenzylideneamino)phenyl)benzamide (3 mmol) in methanol was cooled with an ice bath. Sodium borohydride was added until the color turned white. Excess sodium borohydride was quenched by the addition of distilled water. The resulting mixture was extracted with ethyl acetate (50 mL×3). The combined organics were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuum to obtain N-(5-(pyrrolidin-1-yl)-2-(3,4,5-trimethoxybenzylamino)phenyl)benzamide as a solid.

Workup

  1. temperaturewas cooled with an ice bath
  2. customExcess sodium borohydride was quenched by the addition of distilled water
  3. extractionThe resulting mixture was extracted with ethyl acetate (50 mL×3)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-0959e4e4f5f4469d8cfb8cb7325340a8
Source dataset
uspto-grants-2013_08
Patent number
US08501957B2

Reaction notes

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