m-Chloroperbenzoic acid → HCID 13279932, compound

HRID 1249172Notes

Reaction equation

HRID 1249172 reaction equation
Cl.[CH3:2][S:3][CH2:4][CH2:5][NH:6][CH:7]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:12][CH2:11][CH2:10]1)[CH3:8].ClC1C=CC=C(C(OO)=[O:29])C=1>ClCCl>[CH3:2][S:3]([CH2:4][CH2:5][NH:6][CH:7]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:10][CH2:11][CH2:12]1)[CH3:8])=[O:29]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20225022HCID 20225022, compound

Product 1

HCID 13279932HCID 13279932, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Example 78 in the form of its free base (5.7 g), m-chloroperbenzoic acid (3.7 g-85% purity) and dichloromethane (300 ml) was stirred at ambient temperature for 12 hours. The reaction solution was washed with 5N aqueous sodium hydroxide solution and water and then dried. Evaporation of the solvent gave an oil from which N-[2-(methylsulphinyl)ethyl]-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine was separated by high pressure liquid chromatography. The amine was dissolved in dry ether and hydrogen chloride gas passed through the solution to give a gum which was dissolved in ethyl acetate. Heating this solution to 80° C. caused the precipitation of N-[2-(methylsulphinyl)ethyl]-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 170°-171° C.).

Workup

  1. washThe reaction solution was washed with 5N aqueous sodium hydroxide solution and water
  2. customdried
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b7434bf6c70b49d0bf56e3554ac7fb83
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

Loading…