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

HRID 2166615Notes

Reaction equation

HRID 2166615 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2(O)[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[C:12]([OH:23])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl>>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][NH:18][CH2:19][CH2:20][CH:21]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 155715573-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-3-piperidinol

Product 1

HCID 155715613-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridineYield 58%

Procedure

A mixture of 23.6 g. (74.2 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-3-piperidinol and 400 ml. of 2 N hydrochloric acid is heated at reflux for 2 hours. The reaction is cooled, evaporated and dissolved in excess standard sodium bicarbonate and 400 ml. of dichloromethane. The dichloromethane extract is combined with a second 400 ml. dichloromethane extract of the aqueous phase, dried over magnesium sulfate and evaporated to an oil. Crystallization from ether-pentane gave 13.0 g. (58%) of the title compound.

Workup

  1. additionA mixture of 23.6 g
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction is cooled
  4. customevaporated
  5. dissolutiondissolved in excess standard sodium bicarbonate
  6. extractionThe dichloromethane extract
  7. extractiondichloromethane extract of the aqueous phase
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to an oil
  10. customCrystallization from ether-pentane
  11. customgave 13.0 g

Sources & evidence

ORD record
ord-8dbae7afb1a340d38f9c4612921079c7
Source dataset
uspto-grants-1983_06
Patent number
US04387229

Reaction notes

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