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

HRID 1847183Notes

Reaction equation

HRID 1847183 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-6df6b76fa25b4ada8d8339d591498a3f
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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