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

HRID 1525731Notes

Reaction equation

HRID 1525731 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-805485f5ee074f61a3cf7a7aa66ac45f
Source dataset
uspto-grants-2015_07
Patent number
US09085534B2

Reaction notes

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