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

HRID 63076Notes

Reaction equation

HRID 63076 reaction equation
Cl.[CH3:2][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.[Pd]>[CH3:2][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 867282121-(6-methyl-2H-chromen-4-yl)methanamine hydrochloride

Product 1

HCID 82074935(6-methyl-3,4-dihydro-2H-1-benzopyran-4-yl)methanamineYield 68.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-(6-methyl-2H-chromen-4-yl)methanamine hydrochloride (700 mg, 3.3 mmol) in MeOH (20 mL) and AcOH (2 mL) under N2 was added 10% Pd/C (70 mg) at rt. The suspension was stirred at rt overnight under 50 psi of H2. The reaction was filtered and concentrated. The residue was dissolved in EtOAc and washed with sat. Na2CO3, and the organics were concentrated to give 400 mg (68%) of the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 1.98-2.09 (2H, m), 2.28 (3H, s), 2.80-2.83 (1H, m), 2.88-2.96 (1H, m), 3.09 (1H, dd, J=4.5, 12.6 Hz), 4.17 (2H, t, J=6.3 Hz), 6.73 (1H, d, J=8.4 Hz), 6.91-6.97 (2H, m).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with sat. Na2CO3
  5. concentrationthe organics were concentrated

Sources & evidence

ORD record
ord-04b2d6825f564ee282155d842d77943c
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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