Sodium Hydroxide → 7-Methoxy-1-methyl-8-(2-thienyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 1010758Notes

Reaction equation

HRID 1010758 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[CH3:18][O:17][C:15]1[C:14]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:13][C:9]2[CH:10]([CH3:12])[CH2:11][NH:5][CH2:6][CH2:7][C:8]=2[CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292774HCID 22292774, compound

Product 1

HCID 103335117-Methoxy-1-methyl-8-(2-thienyl)-2,3,4,5-tetrahydro-1H-3-benzazepineYield 86.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-8-(2-thienyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (28 mg, 0.076 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and stirred 0.5 hours at 50 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 18 mg of a yellow oil. 1H NMR (400 MHz, CDCl3) d 7.45 (d, J=4 Hz, 1H), 7.39 (s, 1H), 7.27 (d, J=6 Hz, 1H), 7.07 (dd, J=4, 6 Hz, 1H), 6.71 (s, 1H), 3.90 (s, 3H), 3.1-2.9 (m, 6H), 2.80 (m, 1H), 2.22 (bs, 1H), 1.38 (d, J=7 Hz, 3H). MS calculated for C16H19NOS+H: 274, observed: 274.

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-77fc0025d0ce48f2b14f94e35754e2aa
Source dataset
uspto-grants-2011_07
Patent number
US07977329B2

Reaction notes

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