Ethyl Acetate → HCID 66810209, compound

HRID 2046161Notes

Reaction equation

HRID 2046161 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.[H-].[Na+].[Cl:33]C(OCCCl)=O.[C:40]([O:43][CH2:44][CH3:45])(=[O:42])C>CC1CCCO1>[Cl:8][C:4]1[C:5]([Cl:7])=[CH:6][CH:1]=[CH:2][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[C:24]3[C:23]([CH2:30][CH2:29][C:27](=[O:28])[N:26]3[C:40]([O:43][CH:44]([Cl:33])[CH3:45])=[O:42])=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 123052-Chloroethyl chloroformateHCID 24758Sodium hydrideHCID 60795Aripiprazole

Product 1

HCID 66810209HCID 66810209, compound

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent2×

Procedure

To a suspension of aripiprazole (2.0 g, 4.46 mmol) in 2-methyltetrahydrofuran (50 mL) was added NaH (357 mg, 8.92 mmol). The reaction was stirred overnight at room temperature then chloroethyl chloroformate (1.46 mL, 13.38 mmol) was added. Further 2-methyltetrahydrofuran (10 mL) was added to aid stirring. The reaction was stirred overnight at room temperature. The reaction was cooled to 0° C., diluted with ethyl acetate (50 mL) and quenched with aqueous saturated NaHCO3 (50 mL). The reaction was extracted with ethyl acetate (3×50 mL). The combined organics were dried (MgSO4) and concentrated to give 1-chloroethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (crude yield 2.22 g) as a 3:2 mixture of aripiprazole/product. The product was taken onto the next step without purification.

Workup

  1. stirringstirring
  2. stirringThe reaction was stirred overnight at room temperature
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with aqueous saturated NaHCO3 (50 mL)
  5. extractionThe reaction was extracted with ethyl acetate (3×50 mL)
  6. dry with materialThe combined organics were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-05421fd9318847e4a1cd2c59c46108a7
Source dataset
uspto-grants-2013_11
Patent number
US08592427B2

Reaction notes

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