Sodium Hydroxide → 7-Allyloxy-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2035450Notes

Reaction equation

HRID 2035450 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:21])[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[CH2:18]([O:17][C:15]1[C:14]([Cl:21])=[CH:13][C:9]2[CH:10]([CH3:12])[CH2:11][NH:5][CH2:6][CH2:7][C:8]=2[CH:16]=1)[CH:19]=[CH2:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292782N-trifluoroacetyl-7-allyloxy-8-chloro-1-methyl-2,3,4,5tetrahydro-1H-3-benzazepine

Product 1

HCID 104673597-Allyloxy-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 114.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-trifluoroacetyl-7-allyloxy-8-chloro-1-methyl-2,3,4,5tetrahydro-1H-3-benzazepine (23 mg, 0.066 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and stirred overnight at 20 C. The product mixture was diluted with water (5 mL), extracted twice with EtOAc (5 mL), the combined organic phases were washed with brine (5 mL), dried with Na2SO4 and concentrated to give 19 mg of a white solid. 1H NMR (400 MHz, CD3OD) d 7.12 (s, 1 H), 6.81 (s, 1 H), 6.03 (m, 1 H), 5.43 (d, J=17 Hz, 1 H), 5.24 (d, J=10 Hz, 1 H), 4.57 (d, J=5 Hz, 2 H), 3.1-2.9 (m, 5 H),

Workup

  1. extractionextracted twice with EtOAc (5 mL)
  2. washthe combined organic phases were washed with brine (5 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1c7786193c7440d9bf3b8e972186ee01
Source dataset
uspto-grants-2013_11
Patent number
US08575149B2

Reaction notes

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