Triethylamine → 2-[4-[3-Chloro-4-(hydroxymethyl)phenyl]-1-piperazinyl]-1-(2-furanyl)-1-propanone

HRID 462425노트

반응식

HRID 462425 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH2:14][OH:15].C(N(CC)CC)C.Cl[CH2:24][CH2:25][C:26]([C:28]1[O:29][CH:30]=[CH:31][CH:32]=1)=[O:27]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH:25]([CH3:24])[C:26]([C:28]3[O:29][CH:30]=[CH:31][CH:32]=3)=[O:27])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH2:14][OH:15]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 134571012-Chloro-4-(1-piperazinyl)benzenemethanolHCID 203982953-Chloro-1-(2-furanyl)-1-propanone

생성물 1

HCID 203982932-[4-[3-Chloro-4-(hydroxymethyl)phenyl]-1-piperazinyl]-1-(2-furanyl)-1-propanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

At ~25°, a solution of 2-chloro-4-(1-piperaziny)-benzenemethanol 3.0 g, 13.2 mmole) in 30 ml of tetrahydrofuran and 4 ml of triethylamine was added during five minutes to a solution of 3-chloro-1-(2-furanyl)-1-propanone (2.8 g. 13.3 mmole based on 75% purity). The mixture was stirred at 25° for one hour (a white precipitate formed) and was then heated under reflux for one half hour. The mixture was then filtered and the filtrate was evaporated at reduced pressure (<40°) to give an orange, heavy oil. The oil was triturated at 25° first with petroleum ether (30°-60°; two times, 50 ml) and then with diethyl ether. The orange-brown solid was collected, washed with a little diethyl ether, recrystallized from 25 ml of toluene, and finally triturated with diethyl ether (two times, 20 ml) and dried to give 3.10 g (67%), mp 95°-98° (Table 3).

후처리

  1. customformed) and
  2. temperaturewas then heated
  3. temperatureunder reflux for one half hour
  4. filtrationThe mixture was then filtered
  5. customthe filtrate was evaporated at reduced pressure (<40°)
  6. customto give an orange, heavy oil
  7. customThe oil was triturated at 25° first with petroleum ether (30°-60°; two times, 50 ml)
  8. customThe orange-brown solid was collected
  9. washwashed with a little diethyl ether
  10. customrecrystallized from 25 ml of toluene
  11. customfinally triturated with diethyl ether (two times, 20 ml)
  12. customdried
  13. customto give 3.10 g (67%), mp 95°-98° (Table 3)

출처 및 근거

ORD 기록
ord-c5f0c501628641a79ce448d7bdc60f95
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04515793

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