HCID 85870732, compound → 1-(Propan-2-yl)piperidin-4-amine

HRID 491807Notes

Reaction equation

HRID 491807 reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]1)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 85870732HCID 85870732, compound

Product 1

HCID 31633331-(Propan-2-yl)piperidin-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The crude product (6.32 g) containing benzyl(1-isopropylpiperidin-4-yl)carbamate obtained in Example 382-(1) is dissolved in ethanol (100 ml), and thereto is added 10% palladium on carbon (600 mg), and the mixture is stirred at ambient temperature under hydrogen atmosphere overnight. The insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure, and subjected to azeotropic distillation with toluene. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then chloroform/methanol=20/1, and further 10/1) to give 4-amino-1-isopropylpiperidine (1.90 g). The resulting 4-amino-1-isopropylpiperidine is treated with 4N hydrogen chloride in dioxane to give 4-amino-1-isopropylpiperidine dihydrochloride.

Workup

  1. customThe insoluble materials are removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. distillationsubjected to azeotropic distillation with toluene
  4. customThe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-e416711bb747414d9e293964469e6877
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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