HCID 23035477, compound → HCID 178516503, compound

HRID 649137Notes

Reaction equation

HRID 649137 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 x). 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 x)
  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-2d43d3a7ef5944f78ad9b7be7d67b715
Source dataset
uspto-grants-1988_04
Patent number
US04738969

Reaction notes

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