Isopropanol → HCID 14770070, compound

HRID 1109562Notes

Reaction equation

HRID 1109562 reaction equation
C(N(CCCC)CCCC)CCC.[CH:14]([OH:17])([CH3:16])[CH3:15].[O:18]=[C:19]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27][C:26]([C:35](O)=[O:36])=[C:25]2[N:20]1[CH2:21][CH2:22][C:23]1[CH:40]=[CH:39][S:38][C:24]=12.[I-].C[N+]1C=CC=CC=1Cl>C(Cl)Cl>[O:18]=[C:19]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27][C:26]([C:35]([O:17][CH:14]([CH3:16])[CH3:15])=[O:36])=[C:25]2[N:20]1[CH2:21][CH2:22][C:23]1[CH:40]=[CH:39][S:38][C:24]=12

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 14666689HCID 14666689, compound

Product 1

HCID 14770070HCID 14770070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.1 ml of tri-n-butylamine and 6.1 ml of isopropanol were added to a suspension of 2.0 g of 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylic acid and 3.8 g of N-methyl-2-chloropyridinium iodide in 12.5 ml of methylene chloride, the reaction mixture was stirred under reflux for 24 hours, evaporated in vacuo and the residue was chromatographed on silica gel with toluene/ethyl acetate (9:1). After crystallization from methanol, there was obtained pure isopropyl 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate of m.p. 165.5°166°.

Workup

  1. temperatureunder reflux for 24 hours
  2. customevaporated in vacuo
  3. customthe residue was chromatographed on silica gel with toluene/ethyl acetate (9:1)
  4. customAfter crystallization from methanol

Sources & evidence

ORD record
ord-14e8ec2f5915460e813e773489dd6865
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

Loading…