Hydrochloric Acid → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-methylpiperidine

HRID 26073Notes

Reaction equation

HRID 26073 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[C:12]([OH:22])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:23]=O.Cl.[H][H]>[Pd]>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH3:23])[CH2:17]2)=[C:12]([OH:22])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 155715583-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 155715603-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-methylpiperidineYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 600 mg. (1.98 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-piperidine, 0.78 ml. of 37% formaldehyde, 1.98 ml. of 1N hydrochloric acid and 150 mg. of 5% palladium-on-carbon is hydrogenated under 55 p.s.i. of hydrogen for 1.5 hours. The reaction mixture is filtered through diatomaceous earth and concentrated under reduced pressure. The residue is diluted with 75 ml. of saturated sodium bicarbonate and extracted with two 75 ml. portions of dichloromethane. The combined extract is washed with 75 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to yield 567 mg. (90%) of the title compound as an oil.

Workup

  1. additionA mixture of 600 mg
  2. filtrationThe reaction mixture is filtered through diatomaceous earth
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue is diluted with 75 ml
  5. extractionof saturated sodium bicarbonate and extracted with two 75 ml
  6. extractionThe combined extract
  7. washis washed with 75 ml
  8. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  9. customevaporated
  10. customto yield 567 mg

Sources & evidence

ORD record
ord-91a28c788dff475fa02e40d177983598
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

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