[3,5-Bis(dimethylamino)-4-(piperidin-1-yl)phenyl]methanol → 3,5-Bis(dimethylamino)-4-(piperidin-1-yl)benzaldehyde

HRID 1413756Notes

Reaction equation

HRID 1413756 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([N:17]([CH3:19])[CH3:18])[C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:6][OH:7]>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:20])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([N:17]([CH3:19])[CH3:18])[C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH:6]=[O:7]

Participants

4

Reactant 1

HCID 53863713[3,5-Bis(dimethylamino)-4-(piperidin-1-yl)phenyl]methanol

Product 1

HCID 202904023,5-Bis(dimethylamino)-4-(piperidin-1-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

12.9 G. of 3,5-bis(dimethylamino)-4-piperidinobenzyl alcohol, 17.1 g. of activated manganese dioxide and 80 ml. of chloroform were mixed together and stirred at room temperature for 48 hours. The manganese dioxide was filtered off, washed with chloroform and the chloroform evaporated. After purification over aluminum oxide with benzene and recrystallization from ethanol, there was obtained 3,5-bis(dimethylamino)-4-piperidinobenzaldehyde having a melting point of 114°-116° C.

Workup

  1. filtrationThe manganese dioxide was filtered off
  2. washwashed with chloroform
  3. customthe chloroform evaporated
  4. customAfter purification over aluminum oxide
  5. customwith benzene and recrystallization from ethanol

Sources & evidence

ORD record
ord-955011b6099c40c7bdfc37de029e2cd0
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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