Diethylcarbamoyl chloride → 7-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)quinolin-2-yl diethylcarbamate

HRID 2046151Notes

Reaction equation

HRID 2046151 reaction equation
[CH2:1]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]3[CH:18]=[CH:19][C:20]([NH:22][C:14]=3[CH:13]=2)=[O:21])[CH2:5][CH2:4][N:3]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=2[Cl:30])[CH2:2]1.C(N(CC)CC)C.[CH2:38]([N:40]([CH2:44][CH3:45])[C:41](Cl)=[O:42])[CH3:39]>O1CCCC1>[CH2:38]([N:40]([CH2:44][CH3:45])[C:41](=[O:42])[O:21][C:20]1[CH:19]=[CH:18][C:15]2[C:14](=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]3[CH2:5][CH2:4][N:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=4[Cl:30])[CH2:2][CH2:1]3)=[CH:17][CH:16]=2)[N:22]=1)[CH3:39]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 10114519Dehydroaripiprazole

Product 1

HCID 575015807-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)quinolin-2-yl diethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of dehydro-aripiprazole (1.50 g, 3.36 mmol), triethylamine (1.03 mL, 7.39 mmol), diethyl carbamoyl chloride (1.02 mL) were combined in tetrahydrofuran (30 mL). This was then heated to 100° C. for 6 hours by microwave. The reaction was quenched with water (50 mL) and extracted with dichloromethane (2×100 mL). The combined organics were dried (MgSO4) and concentrated. The crude product was purified by column chromatrography on silica eluting with ethyl acetate to 20% tetrahydrofuran/ethyl acetate to give the product. The product was then triturated with heptane to remove aliphatic impurities and then dried to give Compound-334 (1.54 g) as a light brown oil.

Workup

  1. customThe reaction was quenched with water (50 mL)
  2. extractionextracted with dichloromethane (2×100 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatrography on silica eluting with ethyl acetate to 20% tetrahydrofuran/ethyl acetate
  6. customto give the product
  7. customThe product was then triturated with heptane
  8. customto remove aliphatic impurities
  9. customdried
  10. customto give Compound-334 (1.54 g) as a light brown oil

Sources & evidence

ORD record
ord-5f363e2adfa1404f84f85e9bbf914396
Source dataset
uspto-grants-2013_11
Patent number
US08592427B2

Reaction notes

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