4-Chloroquinoline → HCID 23035475, compound

HRID 1710092Notes

Reaction equation

HRID 1710092 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1>Cl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 691404-ChloroquinolineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 23035475HCID 23035475, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
155 °C

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (13.51 g) and 4-chloroquinoline (4.45 g) were heated with stirring at 155° C. for 21/2 hours. The cooled reaction mixture was dissolved in 2 Normal hydrochloric acid to pH 3-4 and the acidic solution was extracted with ethyl acetate. The aqueous solution was then basified to pH greater than 9 and was extracted with chloroform several times. The combined chloroform extracts were dried and evaporated to dryness to give the title compound as an oil. This was treated with maleic acid in ethanol to afford 4-[3-[3-(piperidinomethyl)phenoxy] propylamino]quinoline dimaleate (8.9 g), m.p. 127°-127.5° C. (recrystallised from isopropanol).

Workup

  1. customThe cooled reaction mixture
  2. extractionthe acidic solution was extracted with ethyl acetate
  3. extractionwas extracted with chloroform several times
  4. dry with materialThe combined chloroform extracts were dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5ba2f54490dc4f2286bef3ed67cca0df
Source dataset
uspto-grants-1990_08
Patent number
US04952589

Reaction notes

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