Water → 1-Benzyl-4-((methylamino)methyl)piperidin-4-ol

HRID 127265

Reaction equation

HRID 127265 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:24][CH2:23][C:17]2([O:21][C:20](=O)[NH:19][CH2:18]2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:7]([N:14]1[CH2:24][CH2:23][C:17]([OH:21])([CH2:18][NH:19][CH3:20])[CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 1998151-Oxa-3,8-diazaspiro(4.5)decan-2-one, 8-benzyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 183513291-Benzyl-4-((methylamino)methyl)piperidin-4-olYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 7 g lithium aluminum hydride and 150 ml tetrahydrofuran under argon is added dropwise over 20 minutes a solution of 24.6 g 8-benzyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one in 150 ml tetrahydrofuran. The mixture is heated at reflux for two hours. The stirred mixture is treated with sequential dropwise additions of 7 ml water, 7 ml 15% sodium hydroxide and 21 ml water. The mixture is filtered and the filter cake is washed with three 200 ml portions of dichloromethane. Evaporation of the combined filtrates affords 23 g of 1-benzyl-4-hydroxy-4-methylaminomethylpiperidine, an oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for two hours
  3. filtrationThe mixture is filtered
  4. washthe filter cake is washed with three 200 ml portions of dichloromethane
  5. customEvaporation of the combined filtrates

Sources & evidence

ORD record
ord-72474edb7717452d8033d31a8b526eee
Source dataset
uspto-grants-1981_03
Patent number
US04255432

Linked notes

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