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

HRID 1614433노트

반응식

HRID 1614433 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30f4ac1c70e842ae962c1b4236d3abbe
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05196606

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