Sodium hydride → 8-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propoxy)-1-nicotinoyl-1,2,3,4-tetrahydroquinoline-trihydrochloride

HRID 231076Notes

Reaction equation

HRID 231076 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]([C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1)[CH2:11][CH2:10][CH2:9]2.[Cl:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH3:39])[CH2:28][CH2:27]1>CN(C)C=O>[ClH:22].[ClH:22].[ClH:22].[CH3:39][O:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[N:29]1[CH2:28][CH2:27][N:26]([CH2:25][CH2:24][CH2:23][O:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]([C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=2)[CH2:11][CH2:10][CH2:9]3)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6226691-(3-Chloropropyl)-4-(2-methoxyphenyl)piperazineHCID 30187391,2,3,4-Tetrahydro-1-(3-pyridylcarbonyl)quinolin-8-ol

Product 1

HCID 200345178-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propoxy)-1-nicotinoyl-1,2,3,4-tetrahydroquinoline-trihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.53 (11.0 mmol) of a 50% strength sodium hydride dispersion is introduced in portions into a solution of 2.54 g (10.0 mmol) of 8-hydroxy-1-nicotinoyl-1,2,3,4-tetrahydroquinoline in 20 ml of anhydrous dimethylformamide and the mixture is subsequently stirred at 40°-50° C. for 30 minutes. After cooling to room temperature, a solution of 4.03 g (15.0 mmol) of 1-(3-chloropropyl)-4-(2-methoxyphenyl)piperazine in 20 ml of anhydrous dimethylformamide is added dropwise and the mixture is subsequently stirred at room temperature for 16 hours. The reaction solution is poured onto 150 ml of ice-water and extracted with methylene chloride and the extracts are washed several times with water, dried and concentrated. The crude product is further purified by column chromatography on silica gel (mobile phase toluene:ethanol 9:1) and converted into the dihydrochloride as described under Example 2(a). The product thus obtained is identical to the product described under 2(a).

Workup

  1. stirringthe mixture is subsequently stirred at room temperature for 16 hours
  2. extractionextracted with methylene chloride
  3. washthe extracts are washed several times with water
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product is further purified by column chromatography on silica gel (mobile phase toluene:ethanol 9:1)
  7. customThe product thus obtained

Sources & evidence

ORD record
ord-9393e4b407154a35ba3fa509557bbd05
Source dataset
uspto-grants-1989_07
Patent number
US04845099

Reaction notes

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