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

HRID 1614433

反応式

HRID 1614433 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 15701545N-(4-methylphenyl)-N-phenyl-benzenemethanamine収率 51%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-30f4ac1c70e842ae962c1b4236d3abbe
出典データセット
uspto-grants-1993_03
特許番号
US05196606

関連ノート

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