Water → N-[1-(3-Dimethylaminopropyl)piperidin-4-yl]-N-methylamine

HRID 492911Notes

Reaction equation

HRID 492911 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=O)OC(C)(C)C)[CH2:9][CH2:8]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:7]1[CH2:8][CH2:9][CH:10]([NH:13][CH3:14])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57677405Tert-butyl[1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamate

Product 1

HCID 23153255N-[1-(3-Dimethylaminopropyl)piperidin-4-yl]-N-methylamineYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl [1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamate (2.73 g) in tetrahydrofuran (30 ml) was stirred in an ice bath, and lithium aluminum hydride (1.04 g) was gradually added thereto. The mixture was stirred under a nitrogen atmosphere, for 15 minutes in an ice bath and for 15 minutes at room temperature. It was further heated to reflux for 7 hours under a nitrogen atmosphere. The reaction mixture was cooled in an ice bath, and then water (1.0 ml), 5N aqueous sodium hydroxide (1.0 ml) and water (5.0 ml) were added thereto in that order and stirring was carried out on ice. The insoluble portion was filtered. The filtrate was concentrated to provide the title compound (1.51 g, 83.2%) as a pale yellow oil.

Workup

  1. temperatureIt was further heated
  2. temperatureto reflux for 7 hours under a nitrogen atmosphere
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. stirringin that order and stirring
  5. filtrationThe insoluble portion was filtered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-71ddb3b7d94949dfad61232b0f225c7d
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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