4-Chloroquinoline → HCID 18918361, compound

HRID 1291822Notes

Reaction equation

HRID 1291822 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 691404-ChloroquinolineHCID 759941-Benzylpiperazine

Product 1

HCID 18918361HCID 18918361, compoundYield 81.8%

Procedure

To a solution of 4-chloroquinoline (3 g) in mixed xylenes (b.p. 137°-144° C.) (25 ml) was added 1-benzylpiperazine (6.46 g). The mixture was heated to reflux with stirring for 20 hours then cooled to room temperature. The precipitate that formed was filtered and washed with xylene. To the combined filtrate and washings was added decolourising charcoal and the mixture was heated to reflux for 20 minutes, cooled and filtered through kieselguhr. The filtrate was evaporated to dryness to yield 1-benzyl-4-(4-quinolinyl)piperazine (4.55 g) as a yellow solid: m.p. 105°-106° C.; NMR (CDCl3) δ 2.75 (4H, m), 3.26 (4H, m), 3.66 (2H, s), 6.84 (1H, d), 7.35 (5H, m), 7.45 (1H, m), 7.65 (1H, m), 8.03 (2H, m), 8.73 (1H, m); m/Z 304 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customThe precipitate that formed
  4. filtrationwas filtered
  5. washwashed with xylene
  6. additionTo the combined filtrate and washings was added
  7. temperaturethe mixture was heated
  8. temperatureto reflux for 20 minutes
  9. temperaturecooled
  10. filtrationfiltered through kieselguhr
  11. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-353d3f39c2a948fb9a4687d233eecafb
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

Loading…