Water → 3-[5-(Phenethylaminomethyl)pyridin-2-yl]benzamide

HRID 561359Notes

Reaction equation

HRID 561359 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:14])=[O:13])=[N:7][CH:8]=1)=O.[CH2:18]([NH2:26])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+].O>CO>[CH2:18]([NH:26][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:14])=[O:13])=[N:7][CH:8]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1001PhenethylamineHCID 4311764Sodium borohydrideHCID 593165483-(5-Formylpyridin-2-yl)benzamide

Product 1

HCID 252164363-[5-(Phenethylaminomethyl)pyridin-2-yl]benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(5-formylpyridin-2-yl)benzamide (40 mg, 0.18 mmol) in MeOH (2.5 mL) was added phenethylamine (27 μL, 0.21 mmol). The mixture was stirred for 16 h before adding sodium borohydride (33 mg, 0.88 mmol). After 16 h water (1 mL) was added and the solvent removed in vacuo. Purification of the residue by column chromatography (0.5% NH3: 5% MeOH:DCM) gave the title compound: RT=2.32 min; m/z (ES+)=332.1 [M+H]+.

Workup

  1. customthe solvent removed in vacuo
  2. customPurification of the residue by column chromatography (0.5% NH3: 5% MeOH:DCM)

Sources & evidence

ORD record
ord-64af31a428534ab1a64e36876a6d87df
Source dataset
uspto-grants-2011_11
Patent number
US08063247B2

Reaction notes

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