Water → HCID 23152981, compound

HRID 2265587Notes

Reaction equation

HRID 2265587 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 under a nitrogen atmosphere in an ice bath. Lithium aluminum hydride (280 mg) was added thereto, followed by stirring in an ice bath for 15 min, then at room temperature for 15 min. The reaction mixture was heated to reflux at 100° C. under a nitrogen atmosphere for 11 hr. The reaction mixture was cooled in an ice bath. Water (2.8 ml), a 5N aqueous solution of sodium hydroxide (2.8 ml) and water (14.0 ml) were added thereto in this order, followed by stirring for 2 hr. Insoluble matter was removed by filtration. The filtrate was concentrated to provide the titled compound as a yellow oil (4.65 g, quantitative).

Workup

  1. waitat room temperature for 15 min
  2. temperatureThe reaction mixture was heated
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. stirringby stirring for 2 hr
  5. customInsoluble matter was removed by filtration
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0a1ed741e3b94a049b5c3fdd86684341
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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