Acetonitrile → HCID 9888392, compound

HRID 1816028Notes

Reaction equation

HRID 1816028 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 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
55 °C

Procedure

A mixture of 600 g of 8-[3-(4-piperidinyl)-1-oxopropyl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-one, 6 L of acetonitrile, 0.3 L of water, 345 g (1.3 equivalent) of potassium carbonate and 278 g (1 equivalent) of 3-fluorobenzyl chloride was stirred at about 55° C. and 12 L of water was added dropwise thereto over about 20 minutes while maintaining about 45° C. The mixture was stirred at about 55° C. for 1.5 hours, and at about 20° C. for 3 hours. Precipitated crystals were separated, and washed with 15 L of water. The wet crystals were suspended in 8.0 L of 10% hydrous methanol-denatured ethanol. The material was dissolved at about 70° C., and passed through a dust-removing filter. The filtrate was stirred at about 20° C. for 1.5 hours, 6.9 L of water was added thereto, and the mixture was stirred at about 20° C. for 3 hours. Crystals were separated, washed with 1.8 L of 50% hydrous methanol-denatured ethanol twice and dried to obtain 0.71 kg (yield 88%) of the desired compound as crystals.

Workup

  1. temperatureover about 20 minutes while maintaining about 45° C
  2. stirringThe mixture was stirred at about 55° C. for 1.5 hours
  3. customPrecipitated crystals
  4. customwere separated
  5. washwashed with 15 L of water
  6. dissolutionThe material was dissolved at about 70° C.
  7. filtrationfilter
  8. stirringThe filtrate was stirred at about 20° C. for 1.5 hours
  9. addition6.9 L of water was added
  10. stirringthe mixture was stirred at about 20° C. for 3 hours
  11. customCrystals were separated
  12. washwashed with 1.8 L of 50% hydrous methanol-
  13. customdried

Sources & evidence

ORD record
ord-5adc3bd0f4e64cb48fb38c3152a108ba
Source dataset
uspto-grants-2005_04
Patent number
US06881842B2

Reaction notes

Loading…