[4-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)phenyl]methanol → 4-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)benzaldehyde

HRID 32248

Reaction equation

HRID 32248 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:12]=2[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:20]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>[O-2].[Mn+4].[O-2].C(Cl)(Cl)Cl>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:12]=2[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:20]2)[CH2:9][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 23142118[4-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)phenyl]methanol

Product 1

HCID 231425004-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)benzaldehydeYield 85.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of the crude product of [4-(4-t-butylcyclohexyl)-3-(4-butylpiperazin-1-yl)phenyl]methanol produced in Example (101a) (294 mg), manganese (IV) oxide (1.3 g, 14.95 mmol) and chloroform (15 mL) was refluxed for 40 minutes. The reaction mixture was filtered and insoluble materials were filtered off. The filtrate was concentrated under reduced pressure to give 249 mg of a crude product of the title compound as an ochre oil. This product was directly used without purification for the following reaction.

Workup

  1. temperaturewas refluxed for 40 minutes
  2. filtrationThe reaction mixture was filtered
  3. filtrationinsoluble materials were filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-449de0b95d344595ad9297220a8b494d
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Linked notes

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