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

HRID 558180Notes

Reaction equation

HRID 558180 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.[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

Participants

4

Reactant 3

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

Product 1

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

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-(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).

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
  7. customyielded light yellow crystals, yield 81.1%

Sources & evidence

ORD record
ord-6078531a22ef4b55bdefc81739923866
Source dataset
uspto-grants-2011_11
Patent number
US08063047B2

Reaction notes

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