Sodium Hydroxide → HCID 10402279, compound

HRID 1010763Notes

Reaction equation

HRID 1010763 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH:12]2[CH2:14][CH2:13]2)[C:9]2[CH:15]=[C:16]([Br:21])[C:17]([O:19][CH3:20])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.[Cl-].[Na+].O>[Br:21][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH:12]3[CH2:14][CH2:13]3)[C:9]=2[CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292775N-Trifluoroacetyl-8-bromo-1-cyclopropyl-7-methoxy-2,3,4,5-tetrahydro 1H-3-benzazepine

Product 1

HCID 10402279HCID 10402279, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of N-trifluoroacetyl-8-bromo-1-cyclopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.014 g, 0.037 mmol) in methanol (1 mL) was treated with 15% aqueous NaOH (1 mL), and stirred for 2 hours at 50 C. The product mixture was diluted with brine (10 mL), extracted twice with EtOAc (10 mL), dried with MgSO4, and concentrated to give 0.008 g of a clear oil. 1H NMR (400 MHz, CD3OD) d 7.26 (s, 1H), 6.78 (s, 1H), 3.83 (s, 3H), 3.02 (m, 2H), 2.92 (m, 2H), 2.67 (s, 2H), 0.91 (m, 2H), 0.85 (m, 2H). MS calculated for C13H16BrNO+H: 282, observed: 282.

Workup

  1. extractionextracted twice with EtOAc (10 mL)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9fdf87345eff45c6b0912bfaa3bc9cd0
Source dataset
uspto-grants-2011_07
Patent number
US07977329B2

Reaction notes

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