Toluene → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-4-(3-phenylpropyl)-1,2,5,6-tetrahydropyridine

HRID 26071Notes

Reaction equation

HRID 26071 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[C:21]([CH2:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(O)[CH2:20][CH2:19][NH:18][CH2:17]2)=[C:12]([OH:32])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][NH:18][CH2:19][CH2:20][C:21]=2[CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:12]([OH:32])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 204997883-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-4-(3-phenylpropyl)-4-piperidinol

Product 1

HCID 204997853-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-4-(3-phenylpropyl)-1,2,5,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.0 g. (4.57 mmols.) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-(3-phenylpropyl)-4-piperidinol, 0.95 g. (5.0 mmols.) of p-toluenesulfonic acid monohydrate and 100 ml. of toluene is heated under reflux for 2 hours with a Dean Stark trap. The reaction mixture is cooled and added to 100 ml. of 20% potassium carbonate-200 ml. dichloromethane. The dichloromethane extract along with two additional 200 ml. dichloromethane extracts of the basic phase is dried over magnesium sulfate and evaporated. The residue is crystallized from ether-pentane to yield the title compound.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureunder reflux for 2 hours with a Dean Stark trap
  3. temperatureThe reaction mixture is cooled
  4. additionadded to 100 ml
  5. extractionThe dichloromethane extract along with two additional 200 ml
  6. dry with materialdichloromethane extracts of the basic phase is dried over magnesium sulfate
  7. customevaporated
  8. customThe residue is crystallized from ether-pentane

Sources & evidence

ORD record
ord-44c06bdc24494750aa6f893d13076ba4
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

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