Triethylamine → HCID 544515, compound

HRID 542840Notes

Reaction equation

HRID 542840 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.Br.[CH:25]1([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)CC)C>C1C=CC=CC=1>[CH:25]1([N:31]2[CH2:36][CH2:35][N:34]([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])[CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6120236-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamideHCID 91994591HCID 91994591, compound

Product 1

HCID 544515HCID 544515, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3.7 g (0.01 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide, 3.4 g (0.0105 mole) of 1-cyclo-hexylpiperazine, dihydrobromide, and 4.2 ml (0.03 mole) of triethylamine in 100 ml of benzene was heated under reflux for 40 hr, allowed to cool, filtered and concentrated. The residue was chromatographed over 150 g of silica gel first with dichloromethane and then with 500 ml each of the following solutions of methanol in dichloromethane: 2%, 4%, 6%, 10% and 15%. The fractions containing the product [Rf(silica--75 ethyl acetate:25 methanol:1 triethylamine)=0.6] were concentrated to provide 3.4 g (75%) of clean material and 0.8 g (18%) which was slightly contaminated according to TLC. The contaminated material was combined with 0.8 g of the purer material and recrystallized first from 2-propanol and then from 2-propanol-water to afford 0.7 g (44% recovery) of analytical material, mp 109°-110°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 hr
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed over 150 g of silica gel first with dichloromethane
  7. additionThe fractions containing the product [Rf(silica--75 ethyl acetate:25 methanol:1 triethylamine)=0.6]
  8. concentrationwere concentrated

Sources & evidence

ORD record
ord-449a445b4ee940dea08f68a39accc697
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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