Sodium Hydroxide → 2H-benzazepine

HRID 2421477Notes

Reaction equation

HRID 2421477 reaction equation
N1([C:7]2[CH:17]=[CH:16][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][NH:15][C:9]=3[CH:8]=2)CCOCC1.[OH-].[Na+]>CO>[N:15]1[CH2:14][CH:13]=[CH:12][CH:11]=[C:10]2[CH:16]=[CH:17][CH:7]=[CH:8][C:9]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 669638998-Morpholinobenzazepine

Product 1

HCID 866101862H-benzazepineYield 192.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the N-acetyl benzazepine (0.14 g, 0.40 mmol) from step I above in methanol (10 mL) was added an aqueous 2 N solution of sodium hydroxide (10 mL). The reaction solution was heated under reflux for 72 hours and then cooled to room temperature. The resultant reaction mixture was extracted with dichloromethane, washed with water and aqueous saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue obtained was purified by flash column chromatography (dichloromethane to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide) to give the desired 2H-benzazepine (0.11 g, 89%) as a white foam: 1H NMR (DMSO-d6, 500 MHz) δ 7.35 (t, J=7.5 Hz, 2H), 7.24 (t, J=7.5 Hz, 1H), 7.14 (d, J=7.5 Hz, 2H), 6.84 (d, J=2.5 Hz, 1H), 6.65-6.60 (m, 1H), 6.49-6.38 (br, 1H), 4.33 (d, J=8.5 Hz, 1H), 3.95 (d, J=14.5 Hz, 1H), 3.77 (d, J=14.5 Hz, 1H), 3.71 (t, J=5.0 Hz, 4H), 3.10-2.87 (m, 6H), 2.21-2.12 (m, 1H), 2.03-1.85 (m, 1H).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 72 hours
  3. customThe resultant reaction mixture
  4. extractionwas extracted with dichloromethane
  5. washwashed with water and aqueous saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue obtained
  9. customwas purified by flash column chromatography (dichloromethane to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-41fdae3786c043e0a4b48d2fa2e740dd
Source dataset
uspto-grants-2011_06
Patent number
US07956050B2

Reaction notes

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