Dimethyl Sulfoxide → HCID 20540364, compound

HRID 1065471Notes

Reaction equation

HRID 1065471 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.CS(C)=O.[OH-].[Na+].[C:33]([C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37]Br)#[N:34]>O>[C:33]([C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([NH:11][CH2:12][CH2:13][CH:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:10])=[CH:6][CH:7]=1)#[N:34]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 895992-(Bromomethyl)benzonitrileHCID 130652814-{2-[(3,3-Diphenylpropyl)amino]propyl}phenol

Product 1

HCID 20540364HCID 20540364, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The mixture of 10.0 g 1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 50 ml of dimethylsulfoxide and 2.4 g of sodium hydroxide in 10 ml of water is stirred at 60° for a half hour, whereupon 5.9 g of 2-cyanobenzyl bromide are added and the whole is stirred at room temperature for 20 hours. The mixture is diluted with water, extracted with ethyl acetate & the extract dried and evaporated. The residue is dissolved in the minimum amount of isopropanol, the solution neutralized with isopropanolic oxalic acid and the crude precipitate chromatographed on silica gel, using chloroform eluate, followed by chloroform-methanol (1:1). The initial fraction yields the 1-[4-(2-cyanobenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane, showing I. R. bands at 2220 and 907 cm-1, and the second fraction the 1-[4-(2-carbamoylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane, showing I. R. bands at 1655 and 1450 cm-1. The latter amide is taken up in aqueous ammonia, the mixture extracted with ethyl acetate & the extract dried and acidified with ethereal hydrogen chloride, to yield the corresponding hydrochloride melting at about 100° with decomposition.

Workup

  1. additionare added
  2. extractionextracted with ethyl acetate
  3. customthe extract dried
  4. customevaporated
  5. dissolutionThe residue is dissolved in the minimum amount of isopropanol
  6. customthe crude precipitate chromatographed on silica gel

Sources & evidence

ORD record
ord-bba93da0067e46abae7c1fcf1fb30de0
Source dataset
uspto-grants-1982_05
Patent number
US04329367

Reaction notes

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