N,N-dimethyl-2-[methyl-(2-pyridine-4-yl-ethyl)-amino]-acetamide → N,N-dimethyl-2-[methyl-(2-piperidin-4-yl-ethyl)-amino]-acetamide

HRID 2233144Notes

Reaction equation

HRID 2233144 reaction equation
[CH3:1][N:2]([CH3:16])[C:3](=[O:15])[CH2:4][N:5]([CH3:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1>C(O)(=O)C.CCOCC.O=[Pt]=O>[CH3:16][N:2]([CH3:1])[C:3](=[O:15])[CH2:4][N:5]([CH3:14])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

5

Reactant 1

HCID 21081298N,N-dimethyl-2-[methyl-(2-pyridine-4-yl-ethyl)-amino]-acetamide

Product 1

HCID 21081297N,N-dimethyl-2-[methyl-(2-piperidin-4-yl-ethyl)-amino]-acetamide

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Of the crude N,N-dimethyl-2-[methyl-(2-pyridine-4-yl-ethyl)-amino]-acetamide, 44 g are dissolved in 500 ml of glacial acetic acid and hydrogenated with 4 g of PtO2 at ambient temperature under 3 bar H2. After the catalyst has been removed by suction filtering the filtrate is evaporated down. The residue is made alkaline with 50% potassium hydroxide solution while cooling with ice and the product obtained is taken up in ether. The ether solution is dried over sodium sulphate, filtered and the solution is evaporated down. The product is left as a yellow oil. Yield: 42 g

Workup

  1. customAfter the catalyst has been removed by suction
  2. filtrationfiltering the filtrate
  3. customis evaporated down
  4. temperaturewhile cooling with ice
  5. customthe product obtained
  6. dry with materialThe ether solution is dried over sodium sulphate
  7. filtrationfiltered
  8. customthe solution is evaporated down
  9. waitThe product is left as a yellow oil

Sources & evidence

ORD record
ord-b13555c137a94819b2f8dfd4ed37fe04
Source dataset
uspto-grants-2010_05
Patent number
US07709480B2

Reaction notes

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