Sodium Carbonate → HCID 86703345, compound

HRID 2173673Notes

Reaction equation

HRID 2173673 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.[Na+].[Na+].Br[CH:21](Cl)[CH2:22][CH3:23]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][CH2:9][N:8]3[C:7]=2[C:13]=1[CH2:21][CH2:22][CH2:23]3

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 36872Propane, bromochloro-HCID 16244477HCID 16244477, compound

Product 1

HCID 86703345HCID 86703345, compound

Procedure

To a solution of 8-methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine (0.25 g) in bromochloropropane (2 mL), Na2CO3 (0.6 g) was added, and the reaction heated to reflux. After stirring for 18 hours, the heat was removed, the reaction partitioned between water (30 mL) and ether (25 mL), the layers separated, and the organic layer washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by silica gel chromatography (gradient of EtOAc in heptane) to provide the title compound (0.27 g) as a clear oil: 1H NMR (DMSO-d6) δ 6.82 (d, 1H); 6.36 (d, 1H), 3.68 (s, 3H), 3.04-3.00 (m, 2H), 2.89-2.85 (m, 2H), 2.60-2.57 (m, 2H), 2.53-2.49 (m, 2H), 1.70-1.61 (m, 4H), 1.48-1.40 (m, 2H); MS expected 218 (C14H20NO, M+1), found 218.

Workup

  1. temperaturethe reaction heated to reflux
  2. customthe heat was removed
  3. customthe reaction partitioned between water (30 mL) and ether (25 mL)
  4. customthe layers separated
  5. washthe organic layer washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (gradient of EtOAc in heptane)

Sources & evidence

ORD record
ord-d0a6af30f6ad4e9aad7b00944ddf1919
Source dataset
uspto-grants-2015_06
Patent number
US09056885B2

Reaction notes

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