Acetic Acid → HCID 22707892, compound

HRID 397744Notes

Reaction equation

HRID 397744 reaction equation
C1(OC([N:10]2[CH2:15][CH2:14][C:13]([CH3:26])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C(C)C)[CH:17]=3)[CH2:12][CH2:11]2)=O)C=CC=CC=1.Br.C(O)(=O)C>O>[OH:22][C:18]1[CH:17]=[C:16]([C:13]2([CH3:26])[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 53987266HCID 53987266, compound

Product 1

HCID 22707892HCID 22707892, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-methyl-4-(3-(1-methylethoxy)phenyl)-1-piperidinecarboxylic acid phenyl ester (Preparation 52, 2.4 g, 6.80 mmol) in 1:1 47% aqueous hydrobromic acid:glacial acetic acid (8 ml) was heated under reflux for 16 h. The solution was allowed to cool to room temperature and water (5 ml) was added. The aqueous layer was extracted with methyl tert-butyl ether (3×10 ml) to remove phenol as by-product. The pH was adjusted to 10.3-10.5 with 15% w:v aqueous sodium hydroxide solution and the mixture was left at room temperature for 2 h to allow the product to precipitate. After cooling to 0° C. the precipitate was filtered and washed with cold water (5 ml) to give 4-(3-hydroxyphenyl)-4-methylpiperidine as a solid (776 mg, 60%).

Workup

  1. temperatureunder reflux for 16 h
  2. extractionThe aqueous layer was extracted with methyl tert-butyl ether (3×10 ml)
  3. customto remove phenol as by-product
  4. customto precipitate
  5. temperatureAfter cooling to 0° C. the precipitate
  6. filtrationwas filtered
  7. washwashed with cold water (5 ml)

Sources & evidence

ORD record
ord-1254a8e980ff4594b54c284b11df29fe
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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