Pyridine → 7-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)quinolin-2-yl pivalate

HRID 2046155Notes

Reaction equation

HRID 2046155 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.N1C=CC=CC=1.[C:37](Cl)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>ClCCl>[C:37]([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)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 10114519Dehydroaripiprazole

Product 1

HCID 565969357-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)quinolin-2-yl pivalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of dehydro-aripiprazole (1.2 g, 2.7 mmol) in dichloromethane (30 mL) was added pyridine (1 mL), followed by pivaloyl chloride (0.66 mL, 5.4 mmol). The reaction mixture was stirred for 20 hours, then washed with water and dried over MgSO4. After evaporation the residue was co-evaporated with toluene and then further purified on silica eluting with ethyl acetate. After evaporation of the product containing fraction, Compound-316 (0.53 g) was obtained as a colourless oil.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customAfter evaporation the residue
  4. customfurther purified on silica eluting with ethyl acetate
  5. customAfter evaporation of the product
  6. additioncontaining fraction
  7. customCompound-316 (0.53 g) was obtained as a colourless oil

Sources & evidence

ORD record
ord-e13a4f7e7c7b47188f5fe37c1d344681
Source dataset
uspto-grants-2013_11
Patent number
US08592427B2

Reaction notes

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