Phenethylamine → N-[2-(Phenylsulfonyl)ethyl]benzeneethanamine, hydrochloride hemihydrate

HRID 745172

Reaction equation

HRID 745172 reaction equation
[Cl:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[CH2:13]([NH2:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.CCOCC>C(#N)C.CO.Cl>[OH2:5].[ClH:1].[C:7]1([S:4]([CH2:3][CH2:2][NH:21][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:7]1([S:4]([CH2:3][CH2:2][NH:21][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[ClH:1]

Participants

8

Reactant 4

HCID 1001PhenethylamineHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 13646((2-Chloroethyl)sulphonyl)benzene

Product 1

HCID 131714769N-[2-(Phenylsulfonyl)ethyl]benzeneethanamine, hydrochloride hemihydrateYield 89.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 70.23 g (0.344 mole) of 2-chloroethylphenylsulfone, 41.92 g (0.343 mole) of phenethylamine and 60 ml of triethylamine in 800 ml of acetonitrile was stirred at room temperature for 18 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 solvent was removed in vacuo to give an oil. This was dissolved in methanol and excess to ethereal hydrogen chloride was added and ether was added. A white solid precipitated to give 68.39 g (60%) of white crystalline solid, m.p. 194°-196° 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. customthe solvent was removed in vacuo
  5. customto give an oil
  6. additionwas added
  7. customA white solid precipitated

Sources & evidence

ORD record
ord-ee976a2410fd422094e3c1c5f08f6515
Source dataset
uspto-grants-1986_07
Patent number
US04597902

Linked notes

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