Water → HCID 19018639, compound

HRID 1110022Notes

Reaction equation

HRID 1110022 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:20]3[C:21]4[C:16]([CH2:17][CH2:18][CH2:19]3)=[CH:15][CH:14]=[CH:13][C:12]=4[C:11]=2[CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][N:31]=3)[CH2:26][CH2:25]2)=[CH:6][CH:5]=1.Br[CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42].O>CN(C)C=O>[CH3:36][C:34]1[CH:33]=[CH:32][N:31]=[C:30]([N:27]2[CH2:26][CH2:25][N:24]([CH2:23][CH2:22][C:11]3[C:12]4=[C:21]5[C:16](=[CH:15][CH:14]=[CH:13]4)[CH2:17][CH2:18][CH2:19][N:20]5[C:10]=3[C:7]3[CH:8]=[CH:9][C:4]([O:3][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:5][CH:6]=3)[CH2:29][CH2:28]2)[CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 10095397HCID 10095397, compound

Product 1

HCID 19018639HCID 19018639, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, 0.25 g of sodium hydride was added to 50 ml of dry dimethylformamide, and the solution was heated to a temperature of 80° C. A solution of 4 g of 2-(4-hydroxyphenyl)-1-{2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]ethyl}-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (preparation see Example 8) in 75 ml of dimethylformamide was then added. The reaction mixture was stirred for 10 minutes, whereupon it assumed a greenish coloration. A solution of 1.6 g of ethyl 4-bromobutyrate in 40 ml of dimethylformamide was then added, and the reaction mixture was heated at 80° C. for 30 minutes. The reaction mixture was worked up by adding water and then extracting with dichloromethane. The organic phase was separated, washed, dried and concentrated. The residue which remained was purified by chromatography on a silica gel column, toluene to which amounts of ethanol increasing to 2% had been added being used as the eluent. 1 g of oily ethyl 4-[4-[1-{2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]ethyl}-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-yl]-phenoxy]-butyrate was obtained.

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 30 minutes
  2. extractionextracting with dichloromethane
  3. customThe organic phase was separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue which remained was purified by chromatography on a silica gel column, toluene to which amounts of ethanol increasing to 2%
  8. additionhad been added

Sources & evidence

ORD record
ord-0f5f03a57a2c4d379bcd5b46bb6febe8
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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