Phenethylamine → HCID 19771928, compound

HRID 1614600Notes

Reaction equation

HRID 1614600 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16](=O)[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25]([NH2:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.C1(S(O)(=O)=O)C=CC=CC=1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([CH:13]2[CH2:14][CH2:15][N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH2:11][CH2:12]2)=[N:33][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 1001PhenethylamineHCID 1438176HCID 1438176, compound

Product 1

HCID 19771928HCID 19771928, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 7371Benzenesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 15.56 g (0.045 mol) of N-benzenesulfonyl-4-(p-fluorobenzoyl)-piperidine, 8.50 g (0.0702 mol) of phenethylamine and 0.20 g (0.0013 mol) of benzenesulfonic acid in 400 mL of toluene was heated at reflux for 111 hr. Water was removed from the reaction mixture with a Dean-Stark trap. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute Na2CO3. The CH2Cl2 solution was dried (MgSO4), and the solvent was removed in vacuo. The residue was recrystallized from ether to give 18.32 g (90.5%) of title compound as a light tan solid, mp 123°-126° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 111 hr
  3. customWater was removed from the reaction mixture with a Dean-Stark trap
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between CH2Cl2 and dilute Na2CO3
  6. dry with materialThe CH2Cl2 solution was dried (MgSO4)
  7. customthe solvent was removed in vacuo
  8. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-d41cb2afb58645efb87cd1a950037396
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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