Sodium Hydroxide → 8-Chloro-7-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1035386Notes

Reaction equation

HRID 1035386 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:18])[C:15]([F:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO>[Cl:18][C:14]1[C:15]([F:17])=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22292798N-Trifluoroacetyl-8-chloro-7-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 99908088-Chloro-7-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 197.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-trifluoroacetyl-8-chloro-7-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (160 mg, 0.22 mmol) in methanol (3 mL) was treated with 15% aqueous NaOH (2 mL), and stirred for 3.5 hours at 25 C. The product mixture was concentrated, extracted 3 times with CH2Cl2 (5 mL), dried with Na2SO4 and concentrated to give 93 mg of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.11 (m, 1 H), 6.85 (m, 1 H), 3.05-2.95 (m, 3 H), 2.95-2.80 (m, 3H), 2.68 (m, 1 H), 2.38 (bm, 1 H), 1.31 (m, 3 H). MS calculated for C11H13ClFN+H: 214, observed: 214.

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-35c9c1518312435eaa1ae82ab0ee550a
Source dataset
uspto-grants-2013_10
Patent number
US08546379B2

Reaction notes

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