Sodium Hydroxide → HCID 13077546, compound

HRID 542845Notes

Reaction equation

HRID 542845 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([NH:23][C:24](=O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][N:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2[CH3:43].[OH-].[Na+]>O1CCCC1.O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][N:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH2:34][CH2:35]3)[CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2[CH3:43]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 13077515HCID 13077515, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13077546HCID 13077546, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A cold (-40°) slurry of 1.7 g (0.0127 mole) of anhydrous aluminum chloride in 50 ml of tetrahydrofuran was added to an equally cold suspension of 1.35 g (0.0355 mole) of lithium aluminum hydride in 30 ml of tetrahydrofuran. The mixture was stirred and allowed to warm to -10°. A solution of 3.3 g (0.0073 mole) of N-(6-methoxy-4-methyl-8-quinolinyl)-6-[4-(2-pyridinyl)-1-piperazinyl]hexanamide, 0.2 hydrate in 100 ml of tetrahydrofuran was added to the mixture dropwise, with stirring. The mixture was stirred for 3 hr, treated with 6.5 ml of 30% sodium hydroxide solution and with enough water to clarify the supernatant, and filtered through Supercel. The filtrate was concentrated in vacuo to remove most of the tetrahydrofuran, diluted with dichloromethane, washed with water, dried and concentrated to dryness. Recrystallization of the residue from 2-propanol afforded 2.1 g (66%) of the title compound, mp 78°-81° .

Workup

  1. temperatureto warm to -10°
  2. stirringwith stirring
  3. stirringThe mixture was stirred for 3 hr
  4. filtrationfiltered through Supercel
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto remove most of the tetrahydrofuran
  7. additiondiluted with dichloromethane
  8. washwashed with water
  9. customdried
  10. concentrationconcentrated to dryness
  11. customRecrystallization of the residue from 2-propanol

Sources & evidence

ORD record
ord-dd005def04ed4125ad05cb17bca053f2
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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