Hexamethylenetetramine → (+/-)-4-[4'-(1-(Dimethylamino)ethyl)phenyl]-2-methylbenzaldehyde

HRID 1645812Notes

Reaction equation

HRID 1645812 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2C)=[CH:7][CH:6]=1)[CH3:4].C1N2CN3CN(C2)CN1C3.F[C:30](F)(F)[C:31]([OH:33])=O>>[CH3:18][N:2]([CH3:1])[CH:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:30]([CH:31]=[O:33])=[C:13]([CH3:14])[CH:12]=2)=[CH:9][CH:10]=1)[CH3:4]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 19742087(+/-)-4'-[1-(Dimethylamino)ethyl]-2-methylbiphenyl

Product 1

HCID 19742078(+/-)-4-[4'-(1-(Dimethylamino)ethyl)phenyl]-2-methylbenzaldehydeYield 52%

Procedure

A mixture of 4.76 g of (±)-4'-[1-(dimethylamino)ethyl]-2-methylbiphenyl, 2.94 g of hexamethylenetetramine and 30 mL of trifluoroacetic acid was heated to boiling under reflux for 5 days. The reaction mixture was then concentrated and treated with 100 mL of ice-water, whereupon it was stirred for 15 minutes, made basic with sodium carbonate and extracted with ether. After evaporation of the ethereal extracts and chromatography of the residue on silica gel with methylene chloride/methanol 9:1 as the elution agent there were obtained 2.8 g (52%) of (±)-4-[4'-(1-(dimethylamino)ethyl)phenyl]-2-methylbenzaldehyde as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 days
  3. concentrationThe reaction mixture was then concentrated
  4. additiontreated with 100 mL of ice-water, whereupon it
  5. extractionextracted with ether
  6. customAfter evaporation of the ethereal extracts and chromatography of the residue on silica gel with methylene chloride/methanol 9:1 as the elution agent

Sources & evidence

ORD record
ord-65a3d038d2be4954b2814d21c413e298
Source dataset
uspto-grants-1993_01
Patent number
US05177067

Reaction notes

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