Acetonitrile → HCID 9888392, compound

HRID 1816031Notes

Reaction equation

HRID 1816031 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([C:11]2[CH:12]=[C:13]3[C:18]4=[C:19]([CH2:21][CH2:22][N:17]4[C:16](=[O:23])[CH2:15][CH2:14]3)[CH:20]=2)=[O:10])[CH2:3][CH2:2]1.C(#N)C.C(=O)([O-])[O-].[K+].[K+].[F:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37]Cl>O>[F:33][C:34]1[CH:35]=[C:36]([CH2:37][N:1]2[CH2:2][CH2:3][CH:4]([CH2:7][CH2:8][C:9]([C:11]3[CH:12]=[C:13]4[C:18]5=[C:19]([CH2:21][CH2:22][N:17]5[C:16](=[O:23])[CH2:15][CH2:14]4)[CH:20]=3)=[O:10])[CH2:5][CH2:6]2)[CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 99743-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 99665448-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Product 1

HCID 9888392HCID 9888392, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
52.5 °C

Procedure

A mixture of 8-[3-(4-piperidinyl)-1-oxopropyl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-one (4 g, 12.8 mmol), acetonitrile (26 mL), water (1.4 mL), potassium carbonate (2.3 g, 16.6 mmol) and 3-fluorobenzyl chloride (1.55 mL, 12.8 mmol) was stirred at about 50 to 55° C. After cooling, water (84 mL) was added dropwise thereto. The mixture was stirred at room temperature for about 1 hour. Precipitated crystals were separated, washed with water (80 mL) and dried to obtain 5.09 g (yield 95%) of the desired compound as crystals.

Workup

  1. temperatureAfter cooling
  2. stirringThe mixture was stirred at room temperature for about 1 hour
  3. customPrecipitated crystals
  4. customwere separated
  5. washwashed with water (80 mL)
  6. customdried

Sources & evidence

ORD record
ord-6c69a32bedcf4a7f9e759ab5f9f67beb
Source dataset
uspto-grants-2005_04
Patent number
US06881842B2

Reaction notes

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