HCID 12254294, compound → HCID 16733877, compound

HRID 1714890Notes

Reaction equation

HRID 1714890 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[N:12]([CH:13]=1)[CH:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4].[Cl:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>O>[ClH:14].[CH2:1]([C:5]1[CH:6]=[C:7]2[N:12]([C:13]=1[C:22]([C:21]1[CH:25]=[CH:26][C:18]([CH2:17][CH2:16][CH2:15][N:12]([CH2:7][CH2:6][CH3:5])[CH2:11][CH2:10][CH3:9])=[CH:19][CH:20]=1)=[O:23])[CH:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 12254294HCID 12254294, compoundHCID 86624859HCID 86624859, compound

Product 1

HCID 16733877HCID 16733877, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 9 g (56 mmoles) of 2-butyl-indolizine and 12.4 g (57 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 sodium carbonate solution, the organic phase was dried over sodium sulphate and concentrated to dryness. Next, it was purified by flash chromatography over silica (eluent: methylene chloride-heptane, 80/20). In this manner, 14 g of the desired compound was obtained in the form of an oil.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with sodium carbonate solution
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. concentrationconcentrated to dryness
  5. customNext, it was purified by flash chromatography over silica (eluent: methylene chloride-heptane, 80/20)

Sources & evidence

ORD record
ord-6254d07bcd9641b5bb5bca2ba1ad83f7
Source dataset
uspto-grants-2010_09
Patent number
US07799799B2

Reaction notes

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