Water → HCID 23152981, compound

HRID 1712637Notes

Reaction equation

HRID 1712637 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=O)OC(C)(C)C)[CH2:8][CH2:7]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:6]1[CH2:7][CH2:8][CH:9]([NH:12][CH3:13])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57470854HCID 57470854, compound

Product 1

HCID 23152981HCID 23152981, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of tert-butyl [1-(2-dimethylaminoacetyl)piperidin-4-yl]carbamate (7.07 g) in tetrahydrofuran (100 ml) was stirred with cooling on ice under a nitrogen atmosphere. Lithium aluminium hydride (280 mg) was added thereto, followed by stirring on an ice bath for 15 minutes, then at room temperature for 15 minutes. The reaction mixture was heated and refluxed under a nitrogen atmosphere at 100° C. for 11 hours. The reaction mixture was cooled on ice. Water (2.8 ml), a 5N aqueous solution of sodium hydroxide (2.8 ml) and water (14.0 ml) was added thereto in this order, followed by stirring for 2 hours. Insoluble matter was removed by filtration. The filtrate was concentrated to give the title compound (4.65 g, quant.) as a yellow oil.

Workup

  1. temperaturewith cooling on ice under a nitrogen atmosphere
  2. waitat room temperature for 15 minutes
  3. temperatureThe reaction mixture was heated
  4. temperatureThe reaction mixture was cooled on ice
  5. stirringby stirring for 2 hours
  6. customInsoluble matter was removed by filtration
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-71e56b8f7a8444ee97fa2a180de0b7fb
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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