HCID 23035477, compound → HCID 178516503, compound

HRID 365106Notes

Reaction equation

HRID 365106 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:25]=[C:24]([O:26]CC)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH2:25][C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 23035477HCID 23035477, compound

Product 1

HCID 178516503HCID 178516503, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-[3-[3-(Piperidinomethyl)phenoxy]propylamino]-4-ethoxyquinoline (liberated from the dimaleate (3.0 g)) was stirred under reflux in concentrated hydrochloric acid (30 ml) for 41/2 hours. The reaction mixture was cooled, reduced in volume by evaporation under reduced pressure, taken to pH 9 (aqueous NaHCO3), washed with ether, and extracted into chloroform (3×). The chloroform extracts were combined, dried (MgSO4), evaporated under reduced pressure and the resultant white oil was treated with hot ethylacetate to give the title compound (0.89 g), m.p. 171°-171.5° C. (recrystallised from methanol).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customreduced in volume by evaporation under reduced pressure
  3. washwashed with ether
  4. extractionextracted into chloroform (3×)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. additionthe resultant white oil was treated with hot ethylacetate
  8. customto give
  9. customthe title compound (0.89 g), m.p. 171°-171.5° C. (recrystallised from methanol)

Sources & evidence

ORD record
ord-b2d5146cafce41ad9984aae128c4349b
Source dataset
uspto-grants-1986_08
Patent number
US04608380

Reaction notes

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