2-Methyltetrahydrofuran → 7-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2-yl dibenzylcarbamate

HRID 2046146Notes

Reaction equation

HRID 2046146 reaction equation
[CH:1]1[CH:2]=[C:3]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]4[CH2:30][CH2:29][C:27](=[O:28])[NH:26][C:24]=4[CH:25]=3)[CH2:11][CH2:10]2)[C:4]([Cl:8])=[C:5]([Cl:7])[CH:6]=1.[CH2:31]([N:38]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:39](Cl)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC1CCCO1>C(OCC)(=O)C.O>[CH2:42]([N:38]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:39](=[O:40])[O:28][C:27]1[CH2:29][CH2:30][C:23]2[C:24](=[CH:25][C:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][N:9]([C:3]4[CH:2]=[CH:1][CH:6]=[C:5]([Cl:7])[C:4]=4[Cl:8])[CH2:10][CH2:11]3)=[CH:21][CH:22]=2)[N:26]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 3

HCID 73012-MethyltetrahydrofuranHCID 60795AripiprazoleHCID 12712012Carbamic chloride, bis(phenylmethyl)-

Product 1

HCID 565969567-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2-yl dibenzylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of aripiprazole (1.5 g, 3.3 mmol), dibenzylcarbamoyl chloride (1.74 g, 6.7 mmol) silver carbonate (3.75 g, 13.4 mmol) and 2-methyltetrahydrofuran (30 mL) was heated at reflux for 4 days. The reaction mixture was cooled, diluted with ethyl acetate and water, and then filtered through celite. The organic phase was separated, dried over MgSO4 and evaporated. The residue obtained was further purified on silica eluting with ethyl acetate/tetrahydrofuran to give after evaporation of the major product containing fractions, Compound-80 (1.02 g) was a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through celite
  5. customThe organic phase was separated
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue obtained
  9. customwas further purified on silica eluting with ethyl acetate/tetrahydrofuran
  10. customto give
  11. customafter evaporation of the major product
  12. additioncontaining fractions, Compound-80 (1.02 g)

Sources & evidence

ORD record
ord-5cf09b555ca4406fabc9da44e6c3b023
Source dataset
uspto-grants-2013_11
Patent number
US08592427B2

Reaction notes

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