Acetonitrile → HCID 86703343, compound

HRID 2173671Notes

Reaction equation

HRID 2173671 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:7]=2[CH:13]=1.C([O-])([O-])=O.[K+].[K+].[C:20](#N)[CH3:21]>ICC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:20][CH3:21])[C:7]=2[CH:13]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 16244477HCID 16244477, compound

Product 1

HCID 86703343HCID 86703343, compound

Reagents, catalysts & solvents 1

HCID 6340IodoethaneSolvent

Procedure

To a solution of 8-methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine (0.5 g) in acetonitrile (25 mL), iodoethane (0.45 mL) and K2CO3 (1.2 g) was added, and the reaction heated to reflux. After stirring for 18 hours, the heat was removed, and the reaction was concentrated. The resulting residue was partitioned between water (30 mL) and EtOAc (25 mL), the layers separated, and the organic layer washed with brine, dried (Na2SO4) and concentrated to provide the title compound (0.54 g) as a clear oil: 1H NMR (DMSO-d6) δ 6.93 (d, 1H); 6.39 (d, 1H), 6.33 (dd, 1H), 3.67 (s, 3H), 3.07 (q, 2H), 2.85-2.82 (m, 2H), 2.62-2.58 (m, 2H), 1.66-1.59 (m, 2H), 1.51-1.43 (m, 2H), 1.10 (t, 3H).

Workup

  1. temperaturethe reaction heated to reflux
  2. customthe heat was removed
  3. concentrationthe reaction was concentrated
  4. customThe resulting residue was partitioned between water (30 mL) and EtOAc (25 mL)
  5. customthe layers separated
  6. washthe organic layer washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-65f70305d4014dacaacef633e715f7e1
Source dataset
uspto-grants-2015_06
Patent number
US09056885B2

Reaction notes

Loading…