Sodium Hydroxide → HCID 57681488, compound

HRID 493411Notes

Reaction equation

HRID 493411 reaction equation
[OH-:1].[Na+].Br[C:4]([CH3:32])([CH3:31])[C:5]([C:7]1[CH:30]=[CH:29][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:28])[C:19]([CH3:27])([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH3:20])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1)=[O:6]>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-].ClCCl.O>[OH:1][C:4]([CH3:32])([CH3:31])[C:5]([C:7]1[CH:30]=[CH:29][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:28])[C:19]([CH3:27])([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH3:20])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1)=[O:6]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67073675HCID 67073675, compound

Product 1

HCID 57681488HCID 57681488, compoundYield 96.8%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalyst2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

5.31 g (0.0664 mol) of 50% NaOH and 175 mg of 50% BTEAC were added to a solution of 17.5 g (0.0369 mol) of 1-{4-[4-(2-bromo-2-methyl-propionyl)-phenoxy]-phenyl}2-methyl-2-morpholin-4-yl-propan-1-one in 35 ml of dichloromethane. The reaction was refluxed for 3 hours, adding 175 mg of BTEAC every hour, then diluted with 20 ml of dichloromethane and 20 ml of water. The organic phase was separated, washed with brine, and dried with sodium sulphate, filtered and evaporated in vacuum obtaining 14.7 g of an oil.

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-2d275e722c484432ac5ea06815a41d17
Source dataset
uspto-grants-2009_05
Patent number
US07534880B2

Reaction notes

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