Piperazine → 1-(Piperazin-1-yl)isoquinoline

HRID 613663

Reaction equation

HRID 613663 reaction equation
Cl[N:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[C:3]1([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][N:2]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 219893902-Chloroisoquinoline

Product 1

HCID 158874361-(Piperazin-1-yl)isoquinolineYield 105.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloroisoquinoline (5 g) in 20 mL of toluene is added dropwise to a refluxing solution of piperazine (20 g) in 150 mL of toluene. The solution is heated for an additional 48 h. After cooling to 0° C. for 0.5 h, the solution is filtered. The filtrate is then extracted with 10% acetic acid. The aqueous extracts are washed with ether, basified and subsequently extracted with dichloromethane. The dichloromethane layer is finally washed with water, dried and concentrated. The material is placed under vacuum overnight to yield the title compound (6.8 g, m.p. 54-56° C.). 1H NMR (CDCl3) 8.14 (d, J=5.5 Hz, 1 H), 8.10 (d, J=8.5 Hz, 1 H), 7.74 (d, J=8.5 Hz, 1 H), 7.60 (t, J=7.2 Hz, 1 H), 7.50 (t, J=7.6 Hz, 1 H), 7.24 (d, J=5.5 Hz, 1 H), 3.39 (t, J=5.0Hz, 4 H), 3.16 (t, J=5.0Hz, 4 H).

Workup

  1. temperatureThe solution is heated for an additional 48 h
  2. filtrationthe solution is filtered
  3. extractionThe filtrate is then extracted with 10% acetic acid
  4. washThe aqueous extracts are washed with ether
  5. extractionbasified and subsequently extracted with dichloromethane
  6. washThe dichloromethane layer is finally washed with water
  7. customdried
  8. concentrationconcentrated
  9. customis placed under vacuum overnight

Sources & evidence

ORD record
ord-c9ee6016525a4416b294225135796a3c
Source dataset
uspto-grants-1999_12
Patent number
US06008352

Linked notes

Loading…