Ethanol → HCID 69742124, compound

HRID 427454Notes

Reaction equation

HRID 427454 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)=O.[CH3:21][C:22]([C:24]1[CH:29]=[CH:28][C:27](OC)=[CH:26][CH:25]=1)=[O:23].[CH2:32](O)C>[OH-].[Na+].[Pd]>[CH3:32][C:27]1[CH:28]=[CH:29][C:24]([C:22]([CH2:21][CH2:1][C:3]2[CH:8]=[CH:7][C:6]([N:9]3[CH2:14][CH2:13][N:12]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)[CH2:11][CH2:10]3)=[CH:5][CH:4]=2)=[O:23])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 702Ethanol2×HCID 74764'-MethoxyacetophenoneHCID 18357052HCID 18357052, compound

Product 1

HCID 69742124HCID 69742124, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 23938PalladiumCatalyst

Procedure

A solution of 1-(4-formylphenyl)-4-(4-pyridyl)piperazine (1.0 g), 4-methoxyacetophenone (503 mg) and concentrated sodium hydroxide (3 drops) in ethanol (25 ml) was stirred at ambient temperature overnight to give a solid which was dissolved in ethanol (100 ml) and hydrogenated over 10% palladium on charcoal to give a solid which was recrystallised from a mixture of ethyl acetate/isohexane to give 1-(4-[4-methylbenzoylethyl]-phenyl)-4-(4-pyridyl)piperazine (400 mg), m.p. 114-115° C.

Workup

  1. customto give a solid which
  2. customto give a solid which
  3. customwas recrystallised from a mixture of ethyl acetate/isohexane

Sources & evidence

ORD record
ord-370c410029594592b2d97218157226ee
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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