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

HRID 558178Notes

Reaction equation

HRID 558178 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]=[N: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]=[N:18][C:17]=1[N:22]1[CH2:27][CH2:26][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)[CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 887471-(2-Pyrimidinyl)piperazineHCID 104433233-Chloro-5,6-dihydrobenzo[h]cinnolineHCID 21905121Ammonium hydrochloride

Product 1

HCID 116817075,6-Dihydro-3-(4-(pyrimidin-2-yl)piperazin-1-yl)benzo[h]cinnolineYield 87%

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-(2-pyrimidyl)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 golden yellow crystals, yield 87.0%; HPLC: 96.6% purity; HRMS calculated 344.1744, found 344.1738; 1H NMR (CDCl3): d 8.452 (d, J=7.5, 1H), 8.346 (d, J=4.5, 2H), 7.200-7.364 (m, 3H), 6.794 (S, 1H), 6.542 (t, J=4.5, 1H), 3.999 (t, J=5.0, 4H), 3.808 (t, J=5.0, 4H), 2.909 (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 golden yellow crystals, yield 87.0%

Sources & evidence

ORD record
ord-f9022d2c66e5479ba01912c4d93efae3
Source dataset
uspto-grants-2011_11
Patent number
US08063047B2

Reaction notes

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