Isopropylamine → N-(1-Methylethyl)-3-(phenylsulfonyl)-1-propanamine hydrochloride

HRID 4194

Reaction equation

HRID 4194 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].[CH:14]([NH2:17])([CH3:16])[CH3:15]>>[ClH:1].[CH3:15][CH:14]([NH:17][CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH3:16]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 11769949(3-Chloropropanesulfonyl)benzene

Product 1

HCID 13655057N-(1-Methylethyl)-3-(phenylsulfonyl)-1-propanamine hydrochloride

Procedure

A solution of 66.55 g (0.3052 mole) of 3-chloropropylphenyl sulfone (prepared by reacting m-chloroperoxybenzoic acid and 3-chloropropyl phenylsulfide in methylene chloride) in 200 ml of isopropylamine was heated at 100° C. overnight in a bomb. The isopropylamine was removed by rotary evaporation and the residue partitioned between chloroform and water. The chloroform layer was extracted with 1N sulfuric acid. The acidic layer was made alkaline and extracted with chloroform. The combined chloroform extract was evaporated to give an oil, the free base of the title compound. The oil was converted to the hydrochloride salt by reacting with ethereal hydrogen chloride. Recrystallization of the precipitated salt from methanol-diethyl ether gave 48.04 g (65.3%) of white crystalline powder, m.p. 185°-186° C.

Workup

  1. customThe isopropylamine was removed by rotary evaporation
  2. customthe residue partitioned between chloroform and water
  3. extractionThe chloroform layer was extracted with 1N sulfuric acid
  4. extractionextracted with chloroform
  5. extractionThe combined chloroform extract
  6. customwas evaporated
  7. customto give an oil

Sources & evidence

ORD record
ord-3899e2d65d6d4b47ba44772811d58aca
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Linked notes

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