Sodium Hydroxide → (5S)-6,7-dichloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 645385Notes

Reaction equation

HRID 645385 reaction equation
FC(F)(F)C([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[C:13]([Cl: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[Cl:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24773647HCID 24773647, compound

Product 1

HCID 11608308(5S)-6,7-dichloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 97.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (S)-N-trifluoroacetyl-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.270 g, 1.2 mmol) in methanol (10 mL) was treated with 15% aqueous NaOH (10 mL), and stirred for 3.5 hours at 25° C. The product mixture was concentrated, extracted 3 times with CH2Cl2 (25 mL), dried with Na2SO4 and concentrated to give 0.270 g of a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.40 (d, J=8 Hz, 1H), 7.16 (d, J=8 Hz, 1H), 4.17 (m, 1H), 3.55 (m, 2H), 3.5-3.3 (m, 2H), 3.2-3.0 (m, 2H), 1.43 (d, J=7 Hz, 3H). MS calculated for C11H13Cl2N+H: 230, observed: 230.

Workup

  1. concentrationThe product mixture was concentrated
  2. extractionextracted 3 times with CH2Cl2 (25 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25231593b8ac4af6ae1ba5619cc10c39
Source dataset
uspto-grants-2010_04
Patent number
US07704993B2

Reaction notes

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