Hydrochloric Acid → N-[2-[(Phenylmethyl)sulfonyl]ethyl]-2-propanamine hydrochloride

HRID 4207Notes

Reaction equation

HRID 4207 reaction equation
[Cl:1][CH2:2][CH2:3][S:4]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])=[O:5].[CH:14]([NH2:17])([CH3:16])[CH3:15].Cl.CCOCC>CO>[ClH:1].[C:8]1([CH2:7][S:4]([CH2:3][CH2:2][NH:17][CH:14]([CH3:16])[CH3:15])(=[O:6])=[O:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6363IsopropylamineHCID 99230(((2-Chloroethyl)sulfonyl)methyl)benzene

Product 1

HCID 13655079N-[2-[(Phenylmethyl)sulfonyl]ethyl]-2-propanamine hydrochlorideYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 51.49 g (0.236 mole) of benzyl 2-chloroethyl sulfone and 600 ml of isopropylamine was stirred at room temperature for 72 hr. The solvent was removed in vacuo, and the residue was partitioned between ether and dilute sodium hydroxide. The ether solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. This was dissolved in methanol, and excess ethereal hydrogen chloride was added. Ether was added, and a white solid precipitated to give 43.11 g (65.8%) of a white crystalline solid, m.p. 180.5°-181.5° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between ether and dilute sodium hydroxide
  3. dry with materialThe ether solution was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto give an oil
  6. customa white solid precipitated

Sources & evidence

ORD record
ord-28031cec7bf3401286c156beffb1ffb3
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Reaction notes

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