Ethanol → 1,4-Bis-(1-anilinoethyl) benzene

HRID 1088520Notes

Reaction equation

HRID 1088520 reaction equation
C([C:4]1[CH:18]=[CH:17][C:7]([N:8]=[C:9]([CH3:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=O)C.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:26](O)[CH3:27]>[Pd]>[NH:19]([CH:26]([C:13]1[CH:12]=[CH:11][C:10]([CH:9]([NH:8][C:7]2[CH:6]=[CH:5][CH:4]=[CH:18][CH:17]=2)[CH3:16])=[CH:15][CH:14]=1)[CH3:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6115AnilineHCID 54464667p-acetyl-N-(alpha-methyl benzylidene) aniline

Product 1

HCID 221631521,4-Bis-(1-anilinoethyl) benzene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of p-acetyl-N-(α-methyl benzylidene) aniline (XXIII) (40 g) prepared by the procedure described in example XXIXA and aniline (20 ml) was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent. The crude product was crystallized from ethanol to give 1,4-Bis-(1-anilinoethyl) benzene (XXV). XXV had a melting point of 169°-170° C.

Workup

  1. customprepared by the procedure
  2. customThe crude product was crystallized from ethanol

Sources & evidence

ORD record
ord-a8bb72a27c534b17b6db7ca974a0ce71
Source dataset
uspto-grants-1990_10
Patent number
US04962234

Reaction notes

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