Water → HCID 71556353, compound

HRID 1497077Notes

Reaction equation

HRID 1497077 reaction equation
C[O:2][C:3]([C:5]1[C:6](Cl)=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][C:9]=2[Cl:22])=[O:4].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.O>N1C=CC=CC=1>[Cl:21][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]([Cl:22])[CH:10]=1)[N:7]=[C:6]([N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:5]([C:3]([OH:2])=[O:4])=[C:14]2[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 86682943HCID 86682943, compound

Product 1

HCID 71556353HCID 71556353, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2,6,8-trichloro-4-phenyl-quinoline-3-carboxylic acid methyl ester (115 mg, 0.314 mmol, Eq: 1.00) and piperidine (150 mg, 174 μl, 1.76 mmol, Eq: 5.6) in pyridine (1.5 ml) was stirred at 135° C. for 3 h in a sealed tube. The solution was allowed to cool to RT and cold water and ice were added. A light yellow solid precipitated which was filtered off, washed with water and dried (42 mg, 6,8-dichloro-4-phenyl-2-piperidin-1-yl-quinoline-3-carboxylic acid methyl ester, MS (ESI): 415.3 (M+H)). The mother liquor was evaporated, water was added to the remaining residue and the pH was adjusted to 2 with 0.1N HCl. The mixture was extracted with chloroform and the combined organic extracts were dried with Na2SO4 and evaporated to yield the title compound (64 mg, yellow solid). MS (ESI): 401.2 (M+H)+.

Workup

  1. customA light yellow solid precipitated which
  2. filtrationwas filtered off
  3. washwashed with water
  4. dry with materialdried (42 mg, 6,8-dichloro-4-phenyl-2-piperidin-1-yl-quinoline-3-carboxylic acid methyl ester, MS (ESI): 415.3 (M+H))
  5. customThe mother liquor was evaporated
  6. additionwater was added to the remaining residue
  7. extractionThe mixture was extracted with chloroform
  8. dry with materialthe combined organic extracts were dried with Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-f6e8018778524465aa853bf6f61c4d1a
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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