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

HRID 2389451Notes

Reaction equation

HRID 2389451 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:18])[CH:16]=[CH:17][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO>[Cl:18][C:15]1[CH:16]=[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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22292812N-trifluoroacetyl-8-chloro-1-ethyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 102422038-Chloro-1-ethyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-trifluoroacetyl-8-chloro-1-ethyl-2,3,4,5-tetrahydro-1H-3-benzazepine (63 mg, 0.207 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and stirred for 3.5 hours at 60 C. The product mixture was concentrated, extracted 3 times with CH2Cl2 (5 mL), dried with Na2SO4 and concentrated to give 35 mg of a clear oil. 1H NMR (400 MHz, DMSO-d6) d 7.2 (m, 3H), 3.3-3.0 (m, 7H), 1.9-1.6 (m, 2H), 0.91 (t, J=7 Hz, 3H). MS calculated for C12H16ClN+H: 210, observed: 210.

Workup

  1. concentrationThe product mixture was concentrated
  2. extractionextracted 3 times with CH2Cl2 (5 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-769f3ad191014029855e343ecb962930
Source dataset
uspto-grants-2012_09
Patent number
US08273734B1

Reaction notes

Loading…