Acetonitrile → HCID 21993914, compound

HRID 1978338Notes

Reaction equation

HRID 1978338 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrCCCC[N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].C(N([CH2:34][CH3:35])CC)C.[C:36](#N)[CH3:37]>>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([CH2:36][CH2:37][CH2:34][CH2:35][C:27]3[CH:26]=[CH:25][CH:24]=[C:21]4[C:22]([NH:18][C:19](=[O:28])[C:20]=34)=[O:23])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 698734-PhenylpiperidineHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 21993914HCID 21993914, compound

Procedure

A solution of 5.00 g (31 mM) of 4-phenylpiperidine, 8.75 g (31 mM) of N-(4-bromobutyl)phthalimide, and 6.5 ml (46.6 mM) of triethylamine in acetonitrile (30 ml) was refluxed under nitrogen for 62 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The resulting crude product was purified by column chromatography (methanol-ethyl acetate 5-10%) to provide the title compound.

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over MgSO4
  6. customThe resulting crude product was purified by column chromatography (methanol-ethyl acetate 5-10%)

Sources & evidence

ORD record
ord-576dbb2b3c7a4652a544c924f89e0f04
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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