Sodium Hydroxide → (1S)-8-Chloro-9-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 645387Notes

Reaction equation

HRID 645387 reaction equation
FC(F)(F)C([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[C:13]([F:18])=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO>[Cl:17][C:14]1[CH:15]=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][C@@H:10]([CH3:12])[C:9]=2[C:13]=1[F:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86613108HCID 86613108, compound

Product 1

HCID 24773897(1S)-8-Chloro-9-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 197.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (S)-N-trifluoroacetyl-8-chloro-9-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) δ 7.06 (dd, J=8, 8 Hz, 1H), 6.75 (d, J=8 Hz, 1H), 3.58 (m, 1H), 3.25-3.15 (m, 3H), 2.93 (d, J=13 Hz, 1H) 2.75-2.60 (m, 3H), 1.96 (bs, 1H), 1.33 (d, J=8 Hz, 3H). 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-7a25a3351ea94af0a4a81579368d776c
Source dataset
uspto-grants-2010_04
Patent number
US07704993B2

Reaction notes

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