Sodium Hydroxide → HCID 28419113, compound

HRID 898531Notes

Reaction equation

HRID 898531 reaction equation
[OH-].[Na+].[CH2:3]([N:5]([CH2:25][CH3:26])[CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([NH:18]C(=O)C(F)(F)F)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[CH3:4]>CO>[CH2:25]([N:5]([CH2:3][CH3:4])[CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86593842HCID 86593842, compound

Product 1

HCID 28419113HCID 28419113, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1.1 mL 6 M aqueous NaOH solution was added to a solution of 0.75 g (2.184 mmol) of N-[1-(2-diethylamino-ethyl)-1,2,3,4-tetrahydro-quinolin-6-yl]-2,2,2-trifluoro-acetamide in 5 mL MeOH at 0° C. and the mixture was stirred for 15 minutes at 0° C. and for 1 hour at RT. The reaction mixture was evaporated down i. vac., sat. aqueous sodium bicarbonate solution was added and the mixture was exhaustively extracted with EtOAc. The combined org. extracts were dried over magnesium sulphate, evaporated down i. vac. and the residue was purified by column chromatography (silica gel, dichloromethane/MeOH/conc. aqueous ammonia 90:10:1).

Workup

  1. customThe reaction mixture was evaporated down i
  2. addition, sat. aqueous sodium bicarbonate solution was added
  3. extractionthe mixture was exhaustively extracted with EtOAc
  4. dry with materialextracts were dried over magnesium sulphate
  5. customevaporated down i
  6. customand the residue was purified by column chromatography (silica gel, dichloromethane/MeOH/conc. aqueous ammonia 90:10:1)

Sources & evidence

ORD record
ord-b88b4475173a4f35b67fb7f1b1b454a5
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

Loading…