Sodium Hydroxide → HCID 10335532, compound

HRID 2108556Notes

Reaction equation

HRID 2108556 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:21])[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:16][C:8]=2[CH2:7][CH:6]1[CH3:22])=O.[OH-].[Na+]>CO.O>[CH2:18]([O:17][C:15]1[C:14]([Br:21])=[CH:13][C:9]2[CH:10]([CH3:12])[CH2:11][NH:5][CH:6]([CH3:22])[CH2:7][C:8]=2[CH:16]=1)[CH:19]=[CH2:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292820N-Trifluoroacetyl-7-allyloxy-8-bromo-1,4-dimethyl-2,3,4,5-tetrahydro 1H-3-benzazepine

Product 1

HCID 10335532HCID 10335532, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-trifluoroacetyl-7-allyloxy-8-bromo-1,4-dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.028 g, 0.069 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and stirred for 3 hours at 20 C. The product mixture was diluted with water (10 mL), extracted twice with EtOAc (10 mL), the combined organic phases were washed with brine (10 mL), dried with Na2SO4 and concentrated to give 0.020 g of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.30 (s, 1H), 6.64 (s, 1H), 6.06 (m, 1H), 5.47 (d, J=17 Hz, 1H), 5.30 (d, J=11 Hz, 1H), 4.56 (s, 2H), 3.03 (m, 2H), 2.90 (dd, J=9, 14 Hz, 1H), 2.80 (m, 1H), 2.65 (d, J=14 Hz, 1H), 2.55 (dd, J=10, 14 Hz, 1H), 1.77 (bs, 1H), 1.30 (d, J=7 Hz, 3H), 1.20 (d, J=6 Hz, 3H).

Workup

  1. extractionextracted twice with EtOAc (10 mL)
  2. washthe combined organic phases were washed with brine (10 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a13d06b25e134fd0aa3bf3d0c48c0124
Source dataset
uspto-grants-2009_04
Patent number
US07514422B2

Reaction notes

Loading…