Triethylamine → HCID 9950564, compound

HRID 1377579Notes

Reaction equation

HRID 1377579 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15](Cl)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1.[C:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:20])[CH3:19].C(N(CC)CC)C.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([N:24]3[CH2:25][CH2:26][N:21]([C:18](=[O:20])[CH3:19])[CH2:22][CH2:23]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 837951-AcetylpiperazineHCID 10778001HCID 10778001, compound

Product 1

HCID 9950564HCID 9950564, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.98 g (7.50 mmole) of 8,11-dichloro-6,11-dihydro-5 H-benzo[5,6]cyclohepta[1,2-b]pyridine, 1.16 g (9.05 mmole) of N-acetylpiperazine, and 2.0 mL of triethylamine in 20 mL of dry THF was refluxed under a nitrogen atmosphere for 16 hr. It was then poured into 5% aqueous sodium hydroxide and extracted three times with methylene chloride. The combined organic portions were dried over MgSO4, filtered and concentrated in vacuo to yield a product which was purified by flash chromatography (5% CH3OH in CHCl3) to afford 1.71 g of the title compound as a glass.

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 16 hr
  2. extractionextracted three times with methylene chloride
  3. dry with materialThe combined organic portions were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a product which
  7. customwas purified by flash chromatography (5% CH3OH in CHCl3)

Sources & evidence

ORD record
ord-848f532d31694b28a5c643a97852ab33
Source dataset
uspto-grants-1997_09
Patent number
US05665726

Reaction notes

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