Sodium Hydroxide → HCID 22504616, compound

HRID 1368941Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:26][CH2:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1>[CH2:29]([O:28][CH2:27][CH2:26][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]([CH3:21])[CH3:22])=[CH:13][CH:12]=1)=[O:10])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The mixture containing 2-(4-chlorophenyl)-1-[4-(2-dimethylaminoethoxy)phenyl]ethanone (6.3 g, 0.020 mol) and TBABr (0.5 g) in toluene (70 ml) is heated to 70° C. and 48% aqueous sodium hydroxide (70 ml) is added. The mixture is stirred for 30 min. and (2-bromoethoxymethyl)benzene (5.5 g, 0.025 mol) is added dropwise at 85-90° C. The reaction mixture is stirred at 95-100° C. for 3 h. The layers are separated and the aqueous phase is extracted with toluene. The combined organic phases are washed with water and the solvent is evaporated. The residual product (9.0 g) is used in the next reaction step without further purification.

Workup

stirringThe reaction mixture is stirred at 95-100° C. for 3 h
customThe layers are separated
extractionthe aqueous phase is extracted with toluene
washThe combined organic phases are washed with water
customthe solvent is evaporated
customThe residual product (9.0 g) is used in the next reaction step without further purification

Sources & evidence

ORD record: ord-e5226fd6ae2349daa4042cb453151fb9
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06576645B1

Reaction notes

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