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

HRID 45995Notes

Reaction equation

HRID 45995 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O.[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([N:27]2[CH2:32][CH2:31][N:30]([CH:33]3[CH2:35][CH2:34]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[CH2:32][CH2:31][N:30]([CH:33]3[CH2:35][CH2:34]3)[CH2:29][CH2:28]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 579895831-Benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidine-4-carbonitrile

Product 1

HCID 57989589(1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)methanamineYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a cooled (0° C.) suspension of LAH (9.24 mmol, 3.0 equiv.) in THF (2 ml/mmol) was added dropwise conc. H2SO4 (4.62 mmol, 1.5 equiv.) in THF (1 ml/mmol) and the resulting suspension was stirred at room temperature for 1.5 h. A solution of 1-benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidine-4-carbonitrile (3.08 mmol, 1.0 equiv.) in THF (2 ml/mmol) was added dropwise to the reaction mixture and it was heated to 50° C. for 12 h. The mixture was quenched with sodium sulfate solution, filtered through celite and washed with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to yield the desired product. Yield: 90%

Workup

  1. temperatureTo a cooled
  2. temperaturewas heated to 50° C. for 12 h
  3. customThe mixture was quenched with sodium sulfate solution
  4. filtrationfiltered through celite
  5. washwashed with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d48b273bd12f467db5d8d52a808b847e
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

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