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Water → HCID 11516277, compound

HRID 743076
Notes
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Reaction equation

HRID 743076 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]=[C:21]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:33]=2[NH2:34])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][CH:21]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:33]=2[NH2:34])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11516226HCID 11516226, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11516277HCID 11516277, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a suspension of 0.68 g (17.9 mmol) of lithium aluminum hydride in 100 mL of tetrahydrofuran was added dropwise a solution of 6.65 g (17.9 mmol) of 3-[α-{(1-benzylpiperidin-4-yl)imino}benzyl]-4-aminopyridine in tetrahydrofuran 30 ml under reflux, and the mixture was heated under reflux for 1 hour. After being cooled, the mixture was added sequentially with 0.7 mL of water, 0.7 mL of an aqueous 15% sodium hydroxide solution and 2 mL of water, under ice-cooling. After being stirred for 1 hour at ambient temperature, the reaction mixture was filtered through cerite. The filtrate was concentrated and the residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform) to give 4.2 g (11.3 mmol) of the title compound.

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperatureAfter being cooled
  5. temperaturecooling
  6. filtrationthe reaction mixture was filtered through cerite
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform)

Sources & evidence

ORD record
ord-063b756c294848609f74b86144edd1a4
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05556860

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes