Sodium Carbonate → HCID 19370298, compound

HRID 129762

Reaction equation

HRID 129762 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C(C)C.[I-].[Na+]>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][CH2:23][N:24]3[C:28](=[O:29])[C:27]4=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]4[C:25]3=[O:34])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 882784-Benzhydrylpiperidine

Product 1

HCID 19370298HCID 19370298, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1.8 g of 4-diphenylmethylpiperidine, 1.92 g of N-(3-bromopropyl)phthalimide, 3.0 g of sodium carbonate and 20 mg of sodium iodide in 70 ml of methyl isobutyl ketone was heated under reflux for 5 hours. At the end of this time, the mixture was cooled to room temperature and filtered. The filtrate was concentrated by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.0 g (yield 95%) of the title compound as crystals, melting at 104°-106° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-c0475da7b76846b6ba4781be5221c883
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Linked notes

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