Sodium Hydroxide → 4-(4-Methylbenzyl)-piperidin-4-ol

HRID 1419906Notes

Reaction equation

HRID 1419906 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][C:9]([OH:20])([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[Na+]>C(O)C.O>[CH3:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:9]2([OH:20])[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 537913684-Hydroxy-4-(4-methyl-benzyl)-piperidin-1-carboxylic acid ethylester

Product 1

HCID 105362424-(4-Methylbenzyl)-piperidin-4-olYield 66.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-carboxylic acid ethylester (70.5 g, 0.25 mol) and sodium hydroxide (26 g, 0.65 mol) in ethanol (350 ml) and water (50 ml) was refluxed for 2 days. Sodium hydroxide (20 g, 0.50 mol) was added and refluxing commenced for another day before cooling to room temperature and evaporating the solvent. The residue was taken up with CH2Cl2 (700 ml) and water (1 l), the organic phase was separated and the water phase extracted with CH2Cl2. The organic phases were pooled, dried with MgSO4 and the solvent was evaporated. The residue was crystallized from n-hexane to give 4-(4-methyl-benzyl)-piperidin-4-ol (34 g, 66%) as an off-white solid, m.p. 118°-121° C. and MS: m/e=206 (M+).

Workup

  1. temperaturewas refluxed for 2 days
  2. temperaturerefluxing
  3. waitcommenced for another day
  4. customevaporating the solvent
  5. customthe organic phase was separated
  6. extractionthe water phase extracted with CH2Cl2
  7. dry with materialdried with MgSO4
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-bebe396b9caf47a1a0b155dbf57d7668
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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