Water → HCID 23153447, compound

HRID 2066168Notes

Reaction equation

HRID 2066168 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 aluminum hydride (405 mg) was suspended in tetrahydrofuran (10 ml) under a nitrogen atmosphere while stirring in an ice water bath, and 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 hr. After the reaction mixture was allowed to cool down to room temperature, water (0.4 ml), a 5N aqueous solution of sodium hydroxide (0.4 ml) and water (1.2 ml) was added thereto, followed by stirring for 13 hr. Insoluble matter in the reaction mixture was filtered through celite, and washed with ethyl acetate (100 ml). The solvent was removed under reduced pressure to provide a crude product of the titled compound as a pale yellow oil (687 mg).

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 3 hr
  2. stirringby stirring for 13 hr
  3. filtrationInsoluble matter in the reaction mixture was filtered through celite
  4. washwashed with ethyl acetate (100 ml)
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f71b4720f49d4c17b07a974f8927460a
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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