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

HRID 444346
Notes
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Reaction equation

HRID 444346 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-5b02977042074c60b1d094b4b376e06f
Source dataset
uspto-grants-1981_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04263438

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes