Sodium Bicarbonate → HCID 23035477, compound

HRID 365105Notes

Reaction equation

HRID 365105 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.C([O-])(O)=O.[Na+]>Cl.O>[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

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 8174292-Chloro-4-ethoxyquinolineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 23035477HCID 23035477, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (9.93 g) and 2-chloro-4-ethoxyquinoline (4.15 g) were heated, with stirring, at 160° C. for 41/4 hours. The reaction mixture was cooled to give a glass which was dissolved in dilute HCl to give a solution having a pH of 6. This solution was washed with diethyl ether (2×), taken to pH 5 and extracted continuously into chloroform. The chloroform extract was evaporated under reduced pressure to give a residue which was dissolved in water, taken to pH 9 with aqueous NaHCO3, and extracted into diethylether (7×) and chloroform (2×). These extracts were dried (MgSO4) and evaporated to give 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]-4-ethoxyquinoline as an oil (7.92 g). This was dissolved in hot ethanol and treated with maleic acid in ethanol to give the dimaleate salt (7.53 g), m.p. 145.5°-147.5° C. (recrystallised from ethanol).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto give a glass which
  3. customto give a solution
  4. washThis solution was washed with diethyl ether (2×)
  5. extractionextracted continuously into chloroform
  6. extractionThe chloroform extract
  7. customwas evaporated under reduced pressure
  8. customto give a residue which
  9. extractionextracted into diethylether (7×) and chloroform (2×)
  10. dry with materialThese extracts were dried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-ba30fdf59f004d75ba1b4a353aa50ada
Source dataset
uspto-grants-1986_08
Patent number
US04608380

Reaction notes

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