4-(Dimethylamino)Benzaldehyde → 2,6-Di-tert-butyl-4-((4-(dimethylamino)phenyl)(piperidin-1-yl)methyl)phenol

HRID 52755

Reaction equation

HRID 52755 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[C:18]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]=1[OH:32])([CH3:21])([CH3:20])[CH3:19].C1(C)C=CC=CC=1.CCCCCC>C1(C)C(C)=CC=CC=1>[C:28]([C:24]1[CH:25]=[C:26]([CH:7]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:6]2[CH:9]=[CH:10][C:3]([N:2]([CH3:11])[CH3:1])=[CH:4][CH:5]=2)[CH:27]=[C:22]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:23]=1[OH:32])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 74794-(Dimethylamino)BenzaldehydeHCID 8082PiperidineHCID 314052,6-Di-tert-butylphenolHCID 21889329Toluene hexane

Product 1

HCID 40667372,6-Di-tert-butyl-4-((4-(dimethylamino)phenyl)(piperidin-1-yl)methyl)phenol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

To 30.4 g (0.2 mol) of 4-dimethylaminobenzaldehyde in 100 ml of xylene, 39.1 g (0.46 mol) of piperidine is added dropwise over a period of six minutes. The mixture is heated at reflux using a Dean-Stark trap until the separation of water is complete. To the cooled reaction mixture 40.3 (0.2 mol) of 2,6-di-tert-butylphenol in 70 ml of xylene is added rapidly. The mixture is then heated at reflux for five hours. The title compound is isolated as an almost white solid by evaporation of the solvent and recrystallization from toluene-hexane. The yield is 66.3 g of the title compound, melting at 184°-185° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. customuntil the separation of water
  4. additionis added rapidly
  5. temperatureThe mixture is then heated
  6. temperatureat reflux for five hours

Sources & evidence

ORD record
ord-beb031635aaa49749c8a2909d1afb736
Source dataset
uspto-grants-1997_04
Patent number
US05616774

Linked notes

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