Dimethyl Sulfoxide → HCID 20540358, compound

HRID 1065466Notes

Reaction equation

HRID 1065466 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([NH:11][CH2:12][CH2:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:10])[CH:5]=[CH:6][CH:7]=1.CS(C)=O.[OH-].[Na+].[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Cl)=[CH:36][CH:35]=1>O>[ClH:33].[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH:9]([NH:11][CH2:12][CH2:13][CH:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH3:10])[CH:5]=[CH:6][CH:7]=2)=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 130652773-[2-[(3,3-Diphenylpropyl)amino]propyl]phenol

Product 1

HCID 20540358HCID 20540358, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 17.3 g of 1-(3-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 100 ml of dimethylsulfoxide and 5 ml of 10 N-aqueous sodium hydroxide is stirred at room temperature for 1/2 hour, combined with 8.05 g of 4-chlorobenzyl chloride and stirred 16 hours longer. It is poured into water, extracted with ethyl acetate, the extract washed with saturated aqueous sodium chloride, dried and evaporated. The residue is taken up in diethyl ether, the solution acidified with isopropanolic hydrogen chloride, the precipitate collected and washed with diethyl ether, to yield the 1-[3-(4-chlorobenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane hydrochloride melting at 184°-189°.

Workup

  1. stirringstirred 16 hours longer
  2. extractionextracted with ethyl acetate
  3. washthe extract washed with saturated aqueous sodium chloride
  4. customdried
  5. customevaporated
  6. customthe precipitate collected
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-5757b4918a3d42b59512b9095102c85b
Source dataset
uspto-grants-1982_05
Patent number
US04329367

Reaction notes

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