Water → HCID 23152981, compound

HRID 492878Notes

Reaction equation

HRID 492878 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 1,020.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl [1-(2-dimethylaminoacetyl)piperidin-4-yl]carbamate (702 mg) in tetrahydrofuran (10.5 ml) was stirred while cooling in an ice bath under a nitrogen atmosphere. Lithium aluminum hydride (280 mg) was added thereto, and the mixture was stirred in an ice bath for 15 minutes and at room temperature for 15 minutes. The reaction mixture was heated to reflux for 11 hours at 100° C. under a nitrogen atmosphere. The reaction mixture was then cooled in an ice bath. Water (2.8 ml), 5N aqueous sodium hydroxide (2.8 ml) and water (14.0 ml) were added in that order, and the mixture was stirred for 2 hours. The insoluble portion was filtered. The filtrate was concentrated to provide the title compound (4.65 g, quantitative) as a yellow oil.

Workup

  1. temperaturewhile cooling in an ice bath under a nitrogen atmosphere
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 11 hours at 100° C. under a nitrogen atmosphere
  4. temperatureThe reaction mixture was then cooled in an ice bath
  5. stirringthe mixture was stirred for 2 hours
  6. filtrationThe insoluble portion was filtered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-055f6ab8658a4867a59da7e1dc6b3299
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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