Phenethylamine → HCID 89837825, 화합물

HRID 1050738노트

반응식

HRID 1050738 반응식
CC(C(N)=O)[C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][C:6]([F:12])=[C:5]([Cl:13])[CH:4]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[CH2:39]([NH2:47])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[N:48]1C=C[CH:51]=[CH:50][CH:49]=1>C(OCC)(=O)C>[Cl:13][C:5]1[CH:4]=[C:3]2[C:8]([C:9](=[O:11])[N:47]([CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:49]([CH2:50][CH3:51])=[N:48]2)=[CH:7][C:6]=1[F:12]

참가 물질

6

반응물 4

HCID 1001PhenethylamineHCID 1049PyridineHCID 7540Triphenyl phosphiteHCID 89837476HCID 89837476, 화합물

생성물 1

HCID 89837825HCID 89837825, 화합물수율 27.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

The crude solid (3 g) from step 3 above mixed with triphenyl phosphite (4 mL, 14.81 mmol) in pyridine (15 mL) was stirred at rt for 4 h. The mixture was added with phenethylamine (1.55 mL, 12.18 mmol), irradiated with microwave 250 W to refluxing for 15 min. The mixture was diluted with ethyl acetate (50 mL), washed with water (2×50 mL). The ethyl acetated solution was mixed with water (50 mL) and kept at rt to give solid form. The solution was filtered to give yellow solid title compound (1.1 g, 27.2%). mp=150-152° C. (recrystallized from ethyl acetate); 1H NMR (400 MHz, DMSO-d6) δ 1.19 (t, J=7.2 Hz, 3H, CH3), 2.76 (q, J=7.2 Hz, 2H, CH2), 2.93 (br t, J=7.6 Hz, 2H, CH2), 4.19 (br t, J=7.6 Hz, 2H, CH2), 7.20-7.31 (m, 5H, ArH), 7.80 (d, J=6.4 Hz, 1H, ArH), 7.91 (d, J=8.8 Hz, 1H, ArH), 13C NMR (100 MHz, DMSO-d6) δ 10.6, 26.9, 33.5, 44.8, 112.2, 112.4, 119.8, 119.9, 126.6, 126.8, 127.0, 128.5, 128.7, 128.8, 138.0, 144.1, 153.6, 156.1, 158.9, 160.0; Anal. (C18H16ClFN2O) C, H, N. Calcd: 65.36, 4.88, 8.47. Found: 65.09, 4.77, 8.50.

후처리

  1. customirradiated with microwave 250 W
  2. temperatureto refluxing for 15 min
  3. washwashed with water (2×50 mL)
  4. additionThe ethyl acetated solution was mixed with water (50 mL)
  5. customkept at rt
  6. customto give solid form
  7. filtrationThe solution was filtered

출처 및 근거

ORD 기록
ord-2ea9c1c789f047f29e2af3a2455dd4da
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09387209B2

반응 노트

불러오는 중…