N,N-Dimethylaminoethyl chloride hydrochloride → 2-[1-(4-chlorophenyl)-1-(3-dimethylamino-4-methoxymethoxyphenyl)methoxy]-N,N-dimethylethanamine

HRID 1032947Notes

Reaction equation

HRID 1032947 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[C:12]([N:20]([CH3:22])[CH3:21])[CH:11]=2)[OH:9])=[CH:4][CH:3]=1.Cl.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.[OH-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[C:12]([N:20]([CH3:21])[CH3:22])[CH:11]=2)[O:9][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 190269591-(4-Chlorophenyl)-1-(3-dimethylamino-4-methoxymethoxyphenyl)methanol

Product 1

HCID 190269862-[1-(4-chlorophenyl)-1-(3-dimethylamino-4-methoxymethoxyphenyl)methoxy]-N,N-dimethylethanamine

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of the compound (1) (1.37 g, 4.26 mmol), 2-(dimethylamino)ethylchloride hydrochloride (1.84 g, 12.3 mmol) and tetrabutylammonium hydrogensulfate (145 mg, 0.43 mmol) in methylene chloride (8.5 ml) and 4N sodium hydroxide (8.5 ml) was stirred under nitrogen atmosphere at room temperature for about 60 hours. The reaction mixture was diluted with water, extracted with methylene chloride, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel to recover the compound (1) (60% recovery) and to give the title compound (2). Yield 0.45 g (30%).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. customto recover the compound (1) (60% recovery)

Sources & evidence

ORD record
ord-c323d034d6f44979948b195a476cb57f
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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