Benzylamine → N-[2-(Phenylsulfonyl)ethyl]benzenemethanamine hydrochloride

HRID 4209

Reaction equation

HRID 4209 reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][Cl:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(#N)C>[ClH:12].[C:1]1([S:7]([CH2:10][CH2:11][NH:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 13646((2-Chloroethyl)sulphonyl)benzene

Product 1

HCID 13655083N-[2-(Phenylsulfonyl)ethyl]benzenemethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 71.90 g (0.352 mole) of 2-chloroethyl phenyl sulfone, 37.45 g (0.350 mole) of benzylamine and 60 ml of triethylamine in 800 ml of acetonitrile was stirred at room temperature for ≈64 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the volume was reduced in vacuo to 300 ml. Methanol was added followed by an excess of ethereal hydrogen chloride. A white precipitate was collected to give 81.30 g (74.5%) of white, crystalline solid, m.p. 211°-213° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  3. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  4. additionMethanol was added
  5. customA white precipitate was collected
  6. customto give 81.30 g (74.5%) of white, crystalline solid, m.p. 211°-213° C.

Sources & evidence

ORD record
ord-81ada1811183440c81eed8afb7279bd4
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Linked notes

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