1-(6-fluoro-2H-chromen-4-yl)methanamine hydrochloride → (6-fluoro-3,4-dihydro-2H-1-benzopyran-4-yl)methanamine

HRID 1847184Notes

Reaction equation

HRID 1847184 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH:7]=[C:6]2[CH2:13][NH2:14]>CO.CC(O)=O.[Ni]>[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][CH:6]2[CH2:13][NH2:14]

Participants

5

Reactant 1

HCID 867282131-(6-fluoro-2H-chromen-4-yl)methanamine hydrochloride

Product 1

HCID 82075091(6-fluoro-3,4-dihydro-2H-1-benzopyran-4-yl)methanamineYield 36%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-(6-fluoro-2H-chromen-4-yl)methanamine hydrochloride (1.36 g, 7.6 mmol) in MeOH (20 mL) and AcOH (10 mL) was added Raney Nickel (760 mg) at room temperature. The suspension was stirred at rt overnight under 50 psi of H2. The reaction mixture was filtered and concentrated. The residue was dissolved in DCM and washed with sat. NaHCO3, dried (Na2SO4), and concentrated to give 490 mg (36%) of the title compound as a green oil. [M+H] calc'd for C10H12FNO, 182. Found 182.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with sat. NaHCO3
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-58d6cd6702e246b7bdfa76bfdadeb4b6
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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