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

HRID 1193345Notes

Reaction equation

HRID 1193345 reaction equation
[CH3:1][N:2]([CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)C(=O)OC(C)(C)C.C([Cl:26])(=O)C>C(O)C>[ClH:26].[ClH:26].[CH3:1][NH:2][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][N:18]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 66805336tert-Butyl methyl((1-(pyrimidin-4-yl)piperidin-4-yl)methyl)carbamate

Product 1

HCID 66798692N-Methyl-1-(1-(pyrimidin-4-yl)piperidin-4-yl)methanamine dihydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butyl methyl((1-(pyrimidin-4-yl)piperidin-4-yl)methyl)carbamate (0.718 mmol, 1 eq) was dissolved in ethanol (2.5 ml), and acetyl chloride (3.59 mmol, 5.0 eq) was added while cooling with ice. The reaction mixture was then stirred for 2 hours at 40° C. and then concentrated. The residue was taken up in a small amount of acetone and a solid was precipitated with diethyl ether. The solid was filtered off, washed with diethyl ether and dried. Yield: >99%

Workup

  1. temperaturewhile cooling with ice
  2. concentrationconcentrated
  3. customa solid was precipitated with diethyl ether
  4. filtrationThe solid was filtered off
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-1d5fad775833418faffb680582c90113
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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