Isopropylamine → N-(1-Methylethyl)-4-(phenylsulfonyl)-1-butanamine hydrochloride

HRID 745173Notes

Reaction equation

HRID 745173 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH:15]([NH2:18])([CH3:17])[CH3:16]>C(Cl)(Cl)Cl.CO>[ClH:1].[CH3:16][CH:15]([NH:18][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:17]

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 12457347((4-Chlorobutyl)sulfonyl)benzene

Product 1

HCID 13655073N-(1-Methylethyl)-4-(phenylsulfonyl)-1-butanamine hydrochlorideYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 105.95 g (0.456 mole) [(4-chlorobutyl)sulfonyl]benzene was heated overnight at 75° C. on an autoclave in 200 ml of isopropylamine. The reaction mixture was stripped to dryness. The residue obtained was dissolved in chloroform and the chloroform layer was extracted with water. The chloroform layer was dried, filtered, and solvent removed to give a dark brown oil. The oil was dissolved in methanol and converted to the hydrochloride salt. This salt was recrystallized from methanol-diethyl ether and dried in vacuo overnight at 80° C. This gave white crystalline product, m.p. 155°-157.5° C. in 30% yield.

Workup

  1. customThe residue obtained
  2. extractionthe chloroform layer was extracted with water
  3. dry with materialThe chloroform layer was dried
  4. filtrationfiltered
  5. customsolvent removed
  6. customto give a dark brown oil
  7. customThis salt was recrystallized from methanol-diethyl ether
  8. customdried in vacuo overnight at 80° C

Sources & evidence

ORD record
ord-5115def2d6364cc7a375d5ae7dc0ffd8
Source dataset
uspto-grants-1986_07
Patent number
US04597902

Reaction notes

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