Sulfuric Acid → HCID 68707356, compound

HRID 645490Notes

Reaction equation

HRID 645490 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O.[ClH:12].[CH3:13][N:14]1[CH2:19][CH2:18][C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:20]#[N:21])[CH2:16][CH2:15]1>C1COCC1>[ClH:12].[ClH:12].[CH3:13][N:14]1[CH2:19][CH2:18][C:17]([CH2:20][NH2:21])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 248859601-Methyl-4-phenylpiperidine-4-carbonitrile--hydrogen chloride (1/1)

Product 1

HCID 68707356HCID 68707356, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of LAH (7.5 mmol) in THF (10 mL) is added dropwise conc. H2SO4 (3.8 mmol) at 0° C. After stirred at 0° C. for 0.5 h, 1-methyl-4-phenylpiperidine-4-carbonitrile hydrochloride (2.5 mmol) is added at 0° C. The reaction mixture is stirred at 60° C. for 6 h. After cooled down to 0° C., the reaction is quenched by the addition of Na2SO4-10H2O. The resulting mixture is filtered through celite, and the filtrate is concentrated in vacuo. The residue is suspended in ether and treated with HCl in 1,4-dioxane. The resulting white solid is collected by filtration to give the title compound, which is directly used for the next reaction without further purification.

Workup

  1. stirringThe reaction mixture is stirred at 60° C. for 6 h
  2. temperatureAfter cooled down to 0° C.
  3. customthe reaction is quenched by the addition of Na2SO4-10H2O
  4. filtrationThe resulting mixture is filtered through celite
  5. concentrationthe filtrate is concentrated in vacuo
  6. additiontreated with HCl in 1,4-dioxane
  7. filtrationThe resulting white solid is collected by filtration

Sources & evidence

ORD record
ord-7317d27a5b354a7994047732e0940f02
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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