Sodium borohydride → HCID 71272171, compound

HRID 475101Notes

Reaction equation

HRID 475101 reaction equation
[CH2:1]([C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[C:18]#[N:19])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH2:18][NH2:19])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86694696HCID 86694696, compound

Product 1

HCID 71272171HCID 71272171, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-ethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrile 6 (7.0 g, 0.027 mol) in dry MeOH (70 mL) at 0° C. was added CoCl2 (5.69 g, 0.043 mol, 1.6 equiv.) and NaBH4 (12.44 g, 0.33 mol, 12 equiv.). The reaction mixture was warmed to RT and stirred for 16 h, then filtered through a Celite® pad and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with 5% MeOH/CHCl3 to afford (4-ethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl) methanamine (5.2 g, 73%) as off white solid.

Workup

  1. filtrationfiltered through a Celite® pad
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by SiO2 chromatography
  4. washeluting with 5% MeOH/CHCl3

Sources & evidence

ORD record
ord-2c7323f30daa442c8a67344d719be1f6
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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