Dimethylamine → HCID 17848809, compound

HRID 1766002Notes

Reaction equation

HRID 1766002 reaction equation
[CH3:1][NH:2][CH3:3].Cl[CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13][CH2:12]2)=[O:8]>ClCCl>[CH3:1][N:2]([CH3:3])[CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13][CH2:12]2)=[O:8]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 17848929HCID 17848929, compound

Product 1

HCID 17848809HCID 17848809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50% Aqueous dimethylamine (51 mL) was added to a solution of ethyl 6-(3-chloropropanoyl)-3,4-dihydro-1(2H)-quinoline carboxylate (15.0 g, 50.7 mmol) obtained in Reference Example 1 in dichloromethane at room temperature and then stirred for 2 hours. The reaction solution was separated, and the organic layer was washed with a saturated saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=1:1), whereby the title compound (16.3 g) was obtained as pale yellow matter.

Workup

  1. customThe reaction solution was separated
  2. washthe organic layer was washed with a saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=1:1), whereby the title compound (16.3 g)
  6. customwas obtained as pale yellow matter

Sources & evidence

ORD record
ord-46d293a158da459d867420267f806269
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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