Water → HCID 23153447, compound

HRID 492988Notes

Reaction equation

HRID 492988 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:11](=O)[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19](=O)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1>[N:7]1([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17][CH2:18]2)[CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23153146HCID 23153146, compound

Product 1

HCID 23153447HCID 23153447, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of lithium aluminum hydride (405 mg) in tetrahydrofuran (10 ml) was stirred while cooling in an ice water bath under a nitrogen atmosphere. 1-(Azetidin-1-yl)-2-(4-benzoylpiperazin-1-yl)ethanone (730 mg) and tetrahydrofuran (5 ml×3) were added thereto. The reaction mixture was stirred at 60° C. for 3 hrs. The reaction mixture was then cooled to room temperature. Water (0.40 ml), 5N aqueous sodium hydroxide (0.40 ml) and water (1.2 ml) were added thereto, and the reaction mixture was stirred for 13 hrs. The reaction mixture was passed through Celite to remove the insoluble material. The insoluble material was washed with ethyl acetate (100 ml). The solvent was evaporated to provide a crude product of the titled compound (687 mg) as a pale yellow oil.

Workup

  1. temperaturewhile cooling in an ice water bath under a nitrogen atmosphere
  2. stirringThe reaction mixture was stirred at 60° C. for 3 hrs
  3. stirringthe reaction mixture was stirred for 13 hrs
  4. customto remove the insoluble material
  5. washThe insoluble material was washed with ethyl acetate (100 ml)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e6c2702a3a284736aab17eee3e21ed3e
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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