2-Chloroquinoline → 1-(2-(2-Quinolinylamino)ethyl)-4-(2-methoxyphenyl)piperazine

HRID 365298Notes

Reaction equation

HRID 365298 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6][CH2:5]1.Cl[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>Cl>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[NH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 119282-ChloroquinolineHCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 232909591-(2-(2-Quinolinylamino)ethyl)-4-(2-methoxyphenyl)piperazineYield 12.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine (9.4 g, 40 mmol) and 2-chloroquinoline (6.5 g, 40 mmol) were heated at 160° C. for 3 h, then at 120° C. for 18 h in a sealed vessel. The resultant brown tar was taken up into dilute hydrochloric acid (300 ml), washed with dichloromethane (3×100 ml) basified with sodium hydroxide, extracted into dichloromethane (3×100 ml), dried (MgSO4) then evaporated in vacuo to give a brown oil. The oil was purified by chromatography [alumina; ethyl acetate-toluene (1:4)] to give the product (1.8 g) as a clear oil.

Workup

  1. washwashed with dichloromethane (3×100 ml)
  2. extractionextracted into dichloromethane (3×100 ml)
  3. dry with materialdried (MgSO4)
  4. customthen evaporated in vacuo
  5. customto give a brown oil
  6. customThe oil was purified by chromatography [alumina; ethyl acetate-toluene (1:4)]

Sources & evidence

ORD record
ord-2e3029fcef974cf897be40ffa1ed8faf
Source dataset
uspto-grants-2000_10
Patent number
US06127357

Reaction notes

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