2-Chloro-4-ethoxyquinoline → HCID 23035477, compound

HRID 2118969Notes

Reaction equation

HRID 2118969 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[CH:29]=[C:28]([O:30][CH2:31][CH3:32])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N: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[CH:29]=[C:28]([O:30][CH2:31][CH3:32])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8174292-Chloro-4-ethoxyquinolineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 23035477HCID 23035477, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (9.93 g) and 2-chloro-4-ethoxyquinoline (4.15 g) were fused at 160° C. for 41/4 hours. The reaction mixture was cooled, dissolved in dilute hydrochloric acid to pH 6 and washed with diethyl ether (2×). The solution was taken to pH 5 and extracted continuously into chloroform. The chloroform extract was evaporated under reduced pressure, dissolved in water, taken to pH 9 with aqueous sodium hydroxide and extracted into diethyl ether (7×) and chloroform (2×). The ether and chloroform extracts were dried (MgSO4) and evaporated to give the title compound as an oil (7.92 g). This was treated with maleic acid in ethanol to give 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]-4-ethoxyquinoline dimaleate (8.24 g), m.p. 145.5°-147.5° C. (recrystallised from ethanol).

Workup

  1. customwere fused at 160° C. for 41
  2. custom4 hours
  3. temperatureThe reaction mixture was cooled
  4. washwashed with diethyl ether (2×)
  5. extractionextracted continuously into chloroform
  6. extractionThe chloroform extract
  7. customwas evaporated under reduced pressure
  8. dissolutiondissolved in water
  9. extractionextracted into diethyl ether (7×) and chloroform (2×)
  10. dry with materialThe ether and chloroform extracts were dried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-8a21e28f425f433f91cefc0d0e999fd6
Source dataset
uspto-grants-1987_07
Patent number
US04681883

Reaction notes

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