Triethylamine → N-[2-(Phenylsulfonyl)ethyl]-1-piperidineethanamine maleate

HRID 330393

Reaction equation

HRID 330393 reaction equation
Cl[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[NH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33]>C(#N)C.CO>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[C:7]1([S:4]([CH2:3][CH2:2][NH:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13646((2-Chloroethyl)sulphonyl)benzeneHCID 33944N-(2-Aminoethyl)piperidineHCID 444266Maleic Acid

Product 1

HCID 70360543N-[2-(Phenylsulfonyl)ethyl]-1-piperidineethanamine maleateYield 60.78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 40.94 g (0.20 mole) of [(2-chloroethyl)sulfonyl]benzene, 27.85 g (0.217 mole) of N-(2-aminoethyl)piperidine and 28.0 g (0.277 mole) of triethylamine in 800 ml of acetonitrile was stirred at room temperature overnight. 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. The residue was dissolved in methanol, a solution of 2 equivalents of maleic acid in methanol was added, and the product crystallized from the solution at room temperatue to give 64.35 g (60.78%) of title compound as a white crystalline solid, mp 154°-155.5° 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. dissolutionThe residue was dissolved in methanol
  6. customthe product crystallized from the solution at room temperatue

Sources & evidence

ORD record
ord-02a04086823f4a4e8450854c0a958793
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Linked notes

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