Acetic Acid → HCID 23000993, compound

HRID 397753Notes

Reaction equation

HRID 397753 reaction equation
C1(OC([N:10]2[CH2:15][CH2:14][C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C(C)C)[CH:20]=3)([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)=O)C=CC=CC=1.Br.C(O)(=O)C>O>[OH:25][C:21]1[CH:20]=[C:19]([C:13]2([CH2:16][CH2:17][CH3:18])[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 53934672HCID 53934672, compound

Product 1

HCID 23000993HCID 23000993, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-(3-(1-methylethoxy)phenyl)-4-n-propyl-1-piperidinecarboxylic acid phenyl ester (Preparation 66, 6.7 g, 17.6 mmol) in 1:1 47% aqueous hydrobromic acid:glacial acetic acid (20 ml) was heated under reflux overnight. The solution was allowed to cool to room temperature and water (10 ml) was added. The aqueous layer was extracted with methyl tert-butyl ether (3×20 ml) to remove phenol as by-product. The aqueous layer was basified with 10M aqueous sodium hydroxide solution. At approximately pH 4, a biphasic solution developed as more methyl tert-butyl ether came out of solution. The layers were separated, and the aqueous layer was further diluted with water (10 ml) to solubilise a red oily deposit. The pH was adjusted to 10.3-10.5 with 10M aqueous sodium hydroxide and the precipitate was filtered and dried in vacuo at 50° C. to give the title compound as a pale brown solid (1.87 g, 48%).

Workup

  1. temperatureunder reflux overnight
  2. extractionThe aqueous layer was extracted with methyl tert-butyl ether (3×20 ml)
  3. customto remove phenol as by-product
  4. customThe layers were separated
  5. additionthe aqueous layer was further diluted with water (10 ml)
  6. filtrationthe precipitate was filtered
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-a26cf084e2bc4049acb1edc40ccce520
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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