Tetrahydrofuran → HCID 71272171, compound

HRID 475089Notes

Reaction equation

HRID 475089 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](=[N:19]O)CC)=[CH:15][C:10]=2[N:9]=[CH:8]1.[CH2:21]1COC[CH2:22]1>[Ni]>[CH2:21]([C:15]1[C:10]2[N:9]=[CH:8][N:7]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[C:11]=2[CH:12]=[CH:13][C:14]=1[CH2:16][NH2:19])[CH3:22]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86694688HCID 86694688, compound

Product 1

HCID 71272171HCID 71272171, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of 1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)propan-1-one oxime (30 mg, 0.11 mmol) in THF (3 mL), Raney-Ni (50 mg) was added. The mixture was stirred at RT overnight. Removal of solvent followed by reverse-phase chromatography gave (4-ethyl-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine (10 mg, 35% yield) as a colorless oil.

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-5c1a312a34174fada403696684c87bee
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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