Sodium Hydroxide → HCID 627160, compound

HRID 542843Notes

Reaction equation

HRID 542843 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:13]=[C:14]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([NH:32][C:33]3[CH:34]=[C:35]([O:44][CH3:45])[CH:36]=[C:37]4[C:42]=3[N:41]=[CH:40][CH:39]=[C:38]4[CH3:43])=O)[CH2:21][CH2:20]2)[CH:15]=[CH:16][C:17]=1[Cl:18].[OH-].[Na+]>O1CCCC1.O>[Cl:11][C:12]1[CH:13]=[C:14]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:32][C:33]3[CH:34]=[C:35]([O:44][CH3:45])[CH:36]=[C:37]4[C:42]=3[N:41]=[CH:40][CH:39]=[C:38]4[CH3:43])[CH2:21][CH2:20]2)[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 13077514HCID 13077514, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 627160HCID 627160, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A cold (-40°) slurry of 0.9 g (0.007 mole) of anhydrous aluminum chloride in 20 ml of dry tetrahydrofuran was added to a cold (-30°) slurry of 0.75 g (0.02 mole) of lithium aluminum hydride in 30 ml of tetrahydrofuran. To the stirred mixture, which had been allowed to warm up to -20°, was added dropwise a solution of 2.7 g (0.0052 mole) of 4-(3,4-dichlorophenyl)-N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide in 30 ml of tetrahydrofuran. The mixture was stirred at -20° -0° for 3 hr, and then treated with 3.3 ml of 30% sodium hydroxide and enough water to clarify the supernatant. The supernatant was decanted from the soft white precipitate which was then washed with additional tetrahydrofuran. The decanted solvent and wash were combined, concentrated in vacuo to remove the tetrahydrofuran, and then combined with water and ether. The ether was washed, dried and concentrated to dryness in vacuo to afford 2.3 g of white solid. Recrystallization from 2-propanol afforded 2.1 g (81%) of the title compound, mp 92°-94°.

Workup

  1. temperatureto warm up to -20°
  2. customThe supernatant was decanted from the soft white precipitate which
  3. washwas then washed with additional tetrahydrofuran
  4. washThe decanted solvent and wash
  5. concentrationconcentrated in vacuo
  6. customto remove the tetrahydrofuran
  7. washThe ether was washed
  8. customdried
  9. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-0744476ffe534def800c5f2cd8d79779
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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