1-(2-Pyridyl)piperazine → 5,6-Dihydro-3-(4-(pyridm-2-yl)piperazin-1-yl)benzo[h]cinnoline

HRID 558180노트

반응식

HRID 558180 반응식
Cl[C:2]1[N:3]=[N:4][C:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][C:10]=2[CH:11]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.Cl.[NH4+]>>[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:23][CH2:24][N:25]([C:2]2[N:3]=[N:4][C:5]3[C:6]4[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=4[CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:26][CH2:27]1

참가 물질

4

반응물 3

HCID 944591-(2-Pyridyl)piperazineHCID 104433233-Chloro-5,6-dihydrobenzo[h]cinnolineHCID 21905121Ammonium hydrochloride

생성물 1

HCID 115882055,6-Dihydro-3-(4-(pyridm-2-yl)piperazin-1-yl)benzo[h]cinnoline수율 81.1%

반응 조건

온도
130 °C

실험 절차

A mixture of comprising about 0.01 mol of 3-chloro-5,6-dihydrobenzo[h]cinnoline, about 0.05 mol of 1-(pyridin-2-yl)piperazine and about 0.01 mol of ammonium hydrochloride was prepared in about 15 ml of 1-BuOH. The mixture was stirred at 130° C. for 48 h, and then the solvent was removed under reduced pressure. The remaining residue was then extracted with ethyl acetate, washed with water and brine, dried over anhydrous Na2SO4. Removal of solvent followed by recrystallization from 95% ethanol yielded light yellow crystals, yield 81.1%; HPLC: 96.4% purity; HRMS calculated 343.1791, found 343.1787; 1H NMR (CDCl3): 5 8.452 (d, J=7.5, 1H), 8.232 (s, 1H), 7.211-7.534 (m, 4H), 6.794 (s, 1H), 6.678-6.731 (m, 2H), 3.862 (d, J=4.0, 4H), 3.745 (d, J=4.0, 4H), 2.918 (s, 4H).

후처리

  1. customthe solvent was removed under reduced pressure
  2. extractionThe remaining residue was then extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customRemoval of solvent
  6. customfollowed by recrystallization from 95% ethanol
  7. customyielded light yellow crystals, yield 81.1%

출처 및 근거

ORD 기록
ord-6078531a22ef4b55bdefc81739923866
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063047B2

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