Water → HCID 23153447, compound

HRID 1712641Notes

Reaction equation

HRID 1712641 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

Lithium aluminium hydride (405 mg) was suspended in tetrahydrofuran (10 ml) under a nitrogen atmosphere with stirring in an ice water bath, 1-(azetidin-1-yl)-2-(4-benzoylpiperazin-1-yl)ethanone (730 mg) and tetrahydrofuran (5 ml×3) was added thereto. The reaction mixture was stirred at 60° C. for 3 hours. The reaction mixture was allowed to cool down to room temperature, and water (0.4 ml), a 5N aqueous solution of sodium hydroxide (0.4 ml) and water (1.2 ml) were added thereto, followed by stirring for 13 hours. The insoluble matter in the reaction mixture was removed by filtration through celite, and washed with ethyl acetate (100 ml). The solvent was distilled off under reduced pressure to give a crude product of the title compound (687 mg) as a pale yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 3 hours
  2. stirringby stirring for 13 hours
  3. customThe insoluble matter in the reaction mixture was removed by filtration through celite
  4. washwashed with ethyl acetate (100 ml)
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b11572b74b2f4483b041f0f82cfa2fcc
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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