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

HRID 558179Notes

Reaction equation

HRID 558179 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
130 °C

Procedure

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).

Workup

  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%

Sources & evidence

ORD record
ord-c98bbbbf772b401eb0a437cc623f47f6
Source dataset
uspto-grants-2011_11
Patent number
US08063047B2

Reaction notes

Loading…