4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrile → (4-Methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamine

HRID 475244Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 162 (9.8 g, 52.5 mmol), MeOH(NH3 in MeOH) and Raney-Ni (>15 eq) 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 (0% to 10% MeOH) to afford 7.0 g (70%) of (4-methyl-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine (164) as yellowish oil: LC/MS: m/z=246 [M+1]+.

Workup

filtrationThe mixture was filtered
concentrationconcentrated in vacuo
customThe crude product was purified by SiO2 chromatography
washeluting with a MeOH/DCM gradient (0% to 10% MeOH)

Sources & evidence

ORD record: ord-e1fb53b1eb674aa4bdee270a43d5d3e2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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