Water → HCID 71268673, compound

HRID 70786Notes

Reaction equation

HRID 70786 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])([C:14]([NH2:16])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:14][NH2:16])([CH3:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 71268660HCID 71268660, compound

Product 1

HCID 71268673HCID 71268673, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A THF (30 ml) solution of 1-benzyl-4-methylpiperidine-4-carboxamide (2.85 g) was added dropwise over 30 minutes to an ice-cooled suspension of LAH (1.40 g) in THF (50 ml) under a flow of argon gas. After beating the reaction to room temperature and stirring for 1 hour, heating and stirring were performed at 50° C. for 1 hour. The reaction liquid was ice-cooled, and a 90% THF aqueous solution (14 mL), a 15% sodium hydroxide aqueous solution (1.4 mL), and water (4.2 mL) were sequentially added. After stirring the reaction liquid at room temperature for 1 hour, Celite filtration was performed, and the filtrate was concentrated under reduced pressure to obtain 1-(1-benzyl-4-methylpiperidin-4-yl)methanamine (2.68 g).

Workup

  1. temperaturecooled
  2. customthe reaction to room temperature
  3. temperatureheating
  4. stirringstirring
  5. waitwere performed at 50° C. for 1 hour
  6. customThe reaction liquid
  7. temperaturecooled
  8. stirringAfter stirring
  9. customthe reaction liquid at room temperature for 1 hour
  10. filtrationCelite filtration
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7b0f285224074bbab3db844dbed19d4c
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

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