Sulfuric Acid → (1-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidin-4-yl)methanamine

HRID 46003

Reaction equation

HRID 46003 reaction equation
OS(O)(=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([N:27]2[CH2:32][CH2:31][N:30]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[CH2:29][CH2:28]2)([C:25]#[N:26])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([CH2:25][NH2:26])([N:27]2[CH2:28][CH2:29][N:30]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[CH2:31][CH2:32]2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 686295031-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidine-4-carbonitrile

Product 1

HCID 57989584(1-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidin-4-yl)methanamineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

H2SO4 (1.5 equiv.) was added to a suspension of LAH (3 equiv.) in THF (32 ml) at 0° C. and the mixture was stirred at room temperature for 0.5 h. A solution of 1-benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidine-4-carbonitrile (5.54 mmol, 1 equiv.) in THF was added under cooled conditions and the resulting reaction mixture was heated to 50° C. for 16 h. The reaction was quenched with THF/H2O solution, filtered and the solid residue washed with excess ethyl acetate. The organic layer was given a brine wash, dried over sodium sulfate and the solvent was removed under reduced pressure. The resulting crude product was used for the next step without further purification. Yield: 85%.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated to 50° C. for 16 h
  3. customThe reaction was quenched with THF/H2O solution
  4. filtrationfiltered
  5. washthe solid residue washed with excess ethyl acetate
  6. washwash
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-50e858841fe74112aab7551f9fc91960
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Linked notes

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