Dimethylformamide → HCID 13002707, compound

HRID 2286231Notes

Reaction equation

HRID 2286231 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:14].[F:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>CCOCC.O>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([CH:22]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[CH3:14])[CH2:24][CH2:23]2)=[O:21])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 130027063-(3-Bromopropyl)-2-methyl-1H-indole

Product 1

HCID 13002707HCID 13002707, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(3-bromopropyl)-2-methylindole (13.8 g), 4-(4-fluorobenzoyl)piperidine (6.0 g), K2CO3 (4.0 g) and dimethylformamide (DMF) (100 ml) is stirred and heated at 50° C. under N2 for 16 hours. The mixture is poured into H2O, and the aqueous mixture extracted with benzene, the benzene extract is washed with H2O, dried (Na2SO4), and the solvent evaporated to leave an oil. The oil is taken up in ether and HCl (g) is bubbled into it to precipitate 10.6 g of a hydrochloride salt. The salt is converted to the free base (an oil). Upon trituration of the oil with ether 4.2 g of a solid is collected. The solid is recrystallized from EtOH-H2O (charcoal treatment), and then twice from isopropanol to yield 1.9 g (15%), m.p. 135°-137° of 3-{3-[4-(4-fluorobenzoyl)piperidyl]propyl} 2-methylindole.

Workup

  1. extractionthe aqueous mixture extracted with benzene
  2. extractionthe benzene extract
  3. washis washed with H2O
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated
  6. customto leave an oil
  7. customHCl (g) is bubbled into it
  8. customto precipitate 10.6 g of a hydrochloride salt
  9. customUpon trituration of the oil with ether 4.2 g of a solid is collected
  10. customThe solid is recrystallized from EtOH-H2O (charcoal treatment)

Sources & evidence

ORD record
ord-ad5c930285a8432bb4a8ebaa0d70d75b
Source dataset
uspto-grants-1982_04
Patent number
US04327103

Reaction notes

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