HCID 71272633, compound → HCID 86694735, compound

HRID 475233Notes

Reaction equation

HRID 475233 reaction equation
[CH3:1][C:2]1[C:3]([C:17]#[N:18])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:6]=2[CH:16]=1>N.CO.[Ni]>[CH3:1][C:2]1[C:3]([CH2:17][NH2:18])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:6]=2[CH:16]=1

Participants

5

Reactant 1

HCID 71272633HCID 71272633, compound

Product 1

HCID 86694735HCID 86694735, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 176 (4.6 g, 19 mmol) Raney-Ni (>15 eq) in 7N NH3 solution in MeOH (10 mL) was stirred under hydrogen at 25° C. for 2 h. The mixture was filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (3 to 5% MeOH) to afford 3.2 g (69%) of (6-methyl-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine (178) as a yellow oil: MS (ESI) m/z=246 [M+1]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by SiO2 chromatography
  4. washeluting with a MeOH/DCM gradient (3 to 5% MeOH)

Sources & evidence

ORD record
ord-f558ac91a4ac4707844f0b051ff026d6
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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