HCID 12254291, compound → HCID 68451359, compound

HRID 1714888Notes

Reaction equation

HRID 1714888 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[N:10]([CH:11]=1)[CH:9]=[CH:8][CH:7]=[CH:6]2)[CH3:2].[Cl:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>O>[CH2:1]([C:3]1[CH:4]=[C:5]2[N:10]([C:11]=1[C:20]([C:19]1[CH:23]=[CH:24][C:16]([CH2:15][CH2:14][CH2:13][Cl:12])=[CH:17][CH:18]=1)=[O:21])[CH:9]=[CH:8][CH:7]=[CH:6]2)[CH3:2]

Participants

4

Reactant 2

HCID 12254291HCID 12254291, compoundHCID 86624859HCID 86624859, compound

Product 1

HCID 68451359HCID 68451359, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8 g (55 mmoles) of 2-ethyl-indolizine and 13.1 g (60 mmoles) of 4-(3-chloropropyl)benzoyl chloride was heated to 50° C. for 18 hours. It was taken up in water, extracted with dichloromethane, washed with a sodium carbonate solution; the organic phase was then dried over sodium sulphate and concentrated to dryness. It was purified by flash chromatography over alumina (eluent: cyclohexane/methylene chloride, 50/50). In this manner, 17 g of the desired compound was obtained in the form of an oil. Yield: 94%.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with a sodium carbonate solution
  3. dry with materialthe organic phase was then dried over sodium sulphate
  4. concentrationconcentrated to dryness
  5. customIt was purified by flash chromatography over alumina (eluent: cyclohexane/methylene chloride, 50/50)

Sources & evidence

ORD record
ord-3282413414764dc49c39198076359fdf
Source dataset
uspto-grants-2010_09
Patent number
US07799799B2

Reaction notes

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