Triethylamine → HCID 13077514, compound

HRID 542842Notes

Reaction equation

HRID 542842 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([O:21][CH3:22])[CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[C:15]2[CH3:20])=[O:8].Br.[Cl:24][C:25]1[CH:26]=[C:27]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:28]=[CH:29][C:30]=1[Cl:31].C(N(CC)CC)C>C1C=CC=CC=1>[Cl:24][C:25]1[CH:26]=[C:27]([N:32]2[CH2:37][CH2:36][N:35]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]3[CH:11]=[C:12]([O:21][CH3:22])[CH:13]=[C:14]4[C:19]=3[N:18]=[CH:17][CH:16]=[C:15]4[CH3:20])=[O:8])[CH2:34][CH2:33]2)[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6120236-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamideHCID 131715102HCID 131715102, compound

Product 1

HCID 13077514HCID 13077514, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.3 g (0.012 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide, 4.0 g (0.0128 mole) of 1-(3,4-dichlorophenyl)piperazine, hydrobromide and 2 ml (0.014 mole) of triethylamine in 100 ml of benzene was heated under reflux for 28 hr, allowed to cool, and filtered to remove the precipitated triethylamine hydrobromide. The filtrate was again heated under reflux for 18 hr, allowed to cool, washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to dryness in vacuo. Chromatography over 200 g of silica gel with first ethyl acetate and then with 10% methanol in ethyl acetate afforded 4.4 g of the desired product, Rf(silica--10% methanol/ethyl acetate)=0.3. Recrystallization from 2-propanol gave 3.8 g (62%), mp 99°-100°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 28 hr
  3. temperatureto cool
  4. filtrationfiltered
  5. customto remove the precipitated triethylamine hydrobromide
  6. temperatureThe filtrate was again heated
  7. temperatureunder reflux for 18 hr
  8. temperatureto cool
  9. washwashed with water and saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-aef09b34c5f047dfbc7443e670eab41d
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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