Dehydroaripiprazole → HCID 58579177, compound

HRID 2046152Notes

Reaction equation

HRID 2046152 reaction equation
[CH2:1]([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]1[N:24]([CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]3[CH:36]=[CH:37][C:38]([NH:40][C:32]=3[CH:31]=2)=[O:39])[CH2:23][CH2:22][N:21]([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[C:42]=2[Cl:48])[CH2:20]1>N1C=CC=CC=1>[CH2:12]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9](=[O:10])[O:39][C:38]1[CH:37]=[CH:36][C:33]2[C:32](=[CH:31][C:30]([O:29][CH2:28][CH2:27][CH2:26][CH2:25][N:24]3[CH2:23][CH2:22][N:21]([C:41]4[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[C:42]=4[Cl:48])[CH2:20][CH2:19]3)=[CH:35][CH:34]=2)[N:40]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 10114519DehydroaripiprazoleHCID 12712012Carbamic chloride, bis(phenylmethyl)-

Product 1

HCID 58579177HCID 58579177, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of dibenzylcarbamoyl chloride (1.7 g, 6.7 mmol) in pyridine (15 mL) was added dehydro-aripiprazole (1.5 g, 3.4 mmol) and the reaction mixture heated at reflux for 4 h. The reaction mixture was concentrated and the residue co-evaporated with toluene (×3). The residue was dissolved in ethyl acetate (ethyl acetate), washed with water and dried over MgSO4. After evaporation the residue was further purified on silica eluting with ethyl acetate and after drying gave Compound-342 (0.71 g) as a white solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 4 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate (ethyl acetate)
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customAfter evaporation the residue
  8. customwas further purified on silica eluting with ethyl acetate
  9. customafter drying
  10. customgave Compound-342 (0.71 g) as a white solid

Sources & evidence

ORD record
ord-c4a13ad9a1bc49e7bb3016de2d52f8e7
Source dataset
uspto-grants-2013_11
Patent number
US08592427B2

Reaction notes

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