1-Phenylpiperazine → 5,6-Dihydro-3-(4-phenylpiperazin-1-yl)benzo[h]cinnoline

HRID 558179노트

반응식

HRID 558179 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.[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.[NH4+]>>[C:16]1([N:22]2[CH2:27][CH2:26][N:25]([C:2]3[N:3]=[N:4][C:5]4[C:6]5[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=5[CH2:8][CH2:9][C:10]=4[CH:11]=3)[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

4

반응물 3

HCID 70961-PhenylpiperazineHCID 104433233-Chloro-5,6-dihydrobenzo[h]cinnolineHCID 21905121Ammonium hydrochloride

생성물 1

HCID 116025935,6-Dihydro-3-(4-phenylpiperazin-1-yl)benzo[h]cinnoline수율 88.1%

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-phenylpiperazine 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 bright yellow crystals, yield 88.1%; HPLC: 96.0% purity; HRMS calculated 342.1839, found 342.1831; 1H NMR (CDCl3): δ 8.474 (d, J=7.5, 1H), 7.222-7.400 (m, 4H), 7.012 (d, J=10, 2H), 6.925 (t, J=6.5, 3=7.5, 1H), 6.824 (S, 1H), 3.900 (s, 4H), 3.370 (d, J=4.5, 4H), 2.932 (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 yielded bright yellow crystals, yield 88.1%

출처 및 근거

ORD 기록
ord-c98bbbbf772b401eb0a437cc623f47f6
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063047B2

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