Acetic Acid → 4-(3-Hydroxyphenyl)piperidine

HRID 397740Notes

Reaction equation

HRID 397740 reaction equation
C1(OC([N:10]2[CH2:15][CH2:14][CH:13]([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.C(O)(=O)C.O>Br>[NH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 537251114-(3-(1-Methylethoxy)phenyl)-1-piperidinecarboxylic acid phenyl ester

Product 1

HCID 105834534-(3-Hydroxyphenyl)piperidineYield 43%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

4-(3-(1-Methylethoxy)phenyl)-1-piperidine-carboxylic acid phenyl ester (Preparation 46, 1.7 g, 5.01 mmol) was heated under reflux in 47% aqueous hydrobromic acid:glacial acetic acid (1:1, 20 ml) for 16 h. The solution was allowed to cool to room temperature and water (10 ml) was added. The solution was extracted with methyl tert-butyl ether (3×10 ml) to remove phenol as a by-product. The pH was adjusted to 10.3-10.5 with 15% w:v aqueous sodium hydroxide solution and the reaction mixture was left at room temperature for 2 h to precipitate the product. After cooling to 0° C. the precipitate was filtered and washed with cold water (5 ml) to give the title compound as a solid (380 mg, 43%).

Workup

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

Sources & evidence

ORD record
ord-a6f9e6ee659343ac9f3a9ad764d79a89
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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