N-Benzylideneaniline → N-(4-methylphenyl)-N-phenyl-benzenemethanamine

HRID 1614433

Reaction equation

HRID 1614433 reaction equation
[CH3:1]C1C=CC(OCC2C=CC=CC=2)=CC=1.C1(C=NC2C=CC=CC=2)C=CC=CC=1.[C:30]1([N:36]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[CH3:1][C:47]1[CH:46]=[CH:45][C:44]([N:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[CH:49][CH:48]=1

Participants

5

Reactant 3

HCID 10858N-BenzylideneanilineHCID 69080BenzyldiphenylamineHCID 70036Benzyl p-tolyl ether

Product 1

HCID 15701545N-(4-methylphenyl)-N-phenyl-benzenemethanamineYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl-4-(phenylmethoxy)benzene (1.98 g, 0.01 mol) and N-(phenylmethylene)benzenamine (1.81 g, 0.01 mol) were reacted in Na/DMF (1 g: 50 mL) at 75° C. for 30 min. Aqueous work-up, extraction with petroleum ether, 3×100 mL, and chromatography with petroleum ether/ethyl acetate 95:5 afforded a total of 1 g. of solid which by HPLC chromatography contained N,N-diphenyl-benzenemethanamine and the title compund in the ratio 6:94 (51% yield by HPLC). The purer fractions from chromatograpy on silica were combined and the solvent removed. The residual oil was dissolved in methanol and some petroleum ether. On cooling this crystallized the title compound. Two recrystallizations from methanol gave the title compund (98.1% pure; 36% yield), mp 85°-6° C. 1H NMR (200 MHz, CDCl3) δ (assignment): 2.29 (s, 3H, methyl), 4.97 (s, 2H, --NCH2Ph), 6.80-6.97 (m, 3H, aromatic) 7.06-7.27 (d, 4H, J=1.37 Hz, --NC6H4CH3), 7.14-7.36 (m, 7H, aromatic). MS [m/e (70 eV, % of base peak)] PhCH2N(Ph)(C6H4)CH3 273 (M+., 96.5), 196 (M+. -Ph., 31.7), 182 (M+. -PhCH3., 100), 167 (M+. -PhCH2. -CH3. 81.2), 91 (C7H7+, 98.3). FTIR (CDCl3): 3089, 3064, 3030, 2924, 2864, 1596, 1572, 1512, 1497, 1453 cm-1.

Workup

  1. extractionAqueous work-up, extraction with petroleum ether, 3×100 mL, and chromatography with petroleum ether/ethyl acetate 95:5
  2. customafforded a total of 1 g
  3. customthe solvent removed
  4. dissolutionThe residual oil was dissolved in methanol
  5. temperatureOn cooling
  6. customthis crystallized the title compound
  7. customTwo recrystallizations from methanol
  8. customgave the title compund (98.1% pure; 36% yield), mp 85°-6° C

Sources & evidence

ORD record
ord-30f4ac1c70e842ae962c1b4236d3abbe
Source dataset
uspto-grants-1993_03
Patent number
US05196606

Linked notes

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