Acetyl chloride → N-Methyl-1-(pyrimidin-4-yl)piperidin-4-amine dihydrochloride

HRID 1193349Notes

Reaction equation

HRID 1193349 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][N:17]=2)[CH2:12][CH2:11]1)C(=O)OC(C)(C)C.C([Cl:25])(=O)C>C(O)C.C(OCC)C>[ClH:25].[ClH:25].[CH3:1][NH:2][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][N:17]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 66805510tert-Butyl methyl(1-(pyrimidin-4-yl)piperidin-4-yl)carbamate

Product 1

HCID 66798935N-Methyl-1-(pyrimidin-4-yl)piperidin-4-amine dihydrochlorideYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butyl methyl(1-(pyrimidin-4-yl)piperidin-4-yl)carbamate (3.63 mmol, 1 eq) was dissolved in ethanol (13 ml), and acetyl chloride (18.13 mmol, 5.0 eq) was added while cooling with ice. The reaction mixture was then stirred for 2 hours at 40° C. The reaction mixture was concentrated under reduced pressure. A white precipitate formed from the concentrated solution. The suspension was diluted with diethyl ether and stirred for 1 hour at RT. Then the precipitate was filtered off with suction, washed with diethyl ether and dried. Yield: 96%

Workup

  1. temperaturewhile cooling with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customA white precipitate formed from the concentrated solution
  4. stirringstirred for 1 hour at RT
  5. filtrationThen the precipitate was filtered off with suction
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-8df638d975c44ca4898e3f215499516e
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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