Sodium Hydroxide → 8-Chloro-1-ethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2035459Notes

Reaction equation

HRID 2035459 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH2:12][CH3:13])[C:9]2[CH:14]=[C:15]([Cl:20])[C:16]([O:18][CH3:19])=[CH:17][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.[Cl-].[Na+].O>[Cl:20][C:15]1[C:16]([O:18][CH3:19])=[CH:17][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH2:12][CH3:13])[C:9]=2[CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292817N-trifluoroacetyl-8-chloro-1-ethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 100601798-Chloro-1-ethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepineYield 80.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of N-trifluoroacetyl-8-chloro-1-ethyl-7-methoxy-2,3,4,5tetrahydro-1H-3-benzazepine (0.421 g, 1.25 mmol) in methanol (30 mL) was treated with 15% aqueous NaOH (30 mL), and stirred overnight at 20 C. The product mixture was diluted with brine (100 mL), extracted twice with EtOAc (200 mL), dried with MgSO4, and concentrated to give 0.241 g of a clear oil. 1H NMR (400 MHz, CD3OD) d 7.05 (s, 1 H), 6.79 (s, 1 H), 3.84 (s, 3 H), 3.03 (m, 3 H), 2.91 (s, 1 H), 2.86-2.76 (m, 3 H), 2.64 (m, 1 H), 1.81 (m, 1 H), 1.72 (m, 1 H), 0.93 (dd, J=8, 8 Hz, 3 H). MS calculated for C13H18clNO+H: 240, observed: 240.

Workup

  1. extractionextracted twice with EtOAc (200 mL)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4a14c2fe79ae416f89b7062884a53888
Source dataset
uspto-grants-2013_11
Patent number
US08575149B2

Reaction notes

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