Dimethyl Sulfoxide → HCID 20540357, compound

HRID 1065468Notes

Reaction equation

HRID 1065468 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:12][CH2:13][CH2:14][CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:11])[CH:5]=[CH:6][C:7]=1[OH:8].CS(C)=O.[OH-].[Na+].[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Cl)=[CH:37][CH:36]=1>O>[ClH:34].[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:12][CH2:13][CH2:14][CH:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH2:39][C:38]1[CH:41]=[CH:42][C:35]([Cl:34])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 13065279HCID 13065279, compound

Product 1

HCID 20540357HCID 20540357, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 7.18 g of 1-(3-methyl-4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 50 ml of dimethylsulfoxide and 2 ml of 10 N-aqueous sodium hydroxide is stirred for 1 hour at 60°. After cooling to room temperature 3.32 g of 4-chlorobenzyl chloride are added and the mixture stirred overnight at said temperature. It is poured into water, extracted with ethyl acetate, the extract dried and evaporated. The residue is taken up in isopropanol, the solution acidified with isopropanolic hydrogen chloride, the precipitate collected and washed with diethyl ether, to yield the 1-[3-methyl-4-(4-chlorobenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane hydrochloride melting at 166°-168°.

Workup

  1. additionare added
  2. stirringthe mixture stirred overnight
  3. extractionextracted with ethyl acetate
  4. customthe extract dried
  5. customevaporated
  6. customthe precipitate collected
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-9423f8226c19498c833384da03f07f49
Source dataset
uspto-grants-1982_05
Patent number
US04329367

Reaction notes

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