Potassium Carbonate → N,N-Dibenzyl-2-(1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl)ethanamine

HRID 1193407Notes

Reaction equation

HRID 1193407 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[C:32]1[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([CH3:39])[N:33]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:24]([N:15]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:16][CH2:17][CH:18]1[CH2:19][CH2:20][N:21]([C:32]2[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([CH3:39])[N:33]=2)[CH2:22][CH2:23]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31541994-Chloro-2,6-dimethylpyrimidineHCID 66799214N,N-dibenzyl-2-(piperidin-4-yl)ethanamine trifluoroacetate

Product 1

HCID 66798939N,N-Dibenzyl-2-(1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl)ethanamineYield 49%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N,N-dibenzyl-2-(piperidin-4-yl)ethanamine trifluoroacetate (see stage 6 AMN-01) (6.372 mmol, 1.0 eq), 4-chloro-2,6-dimethylpyrimidine (1.17 g, 8.283 mmol, 1.3 eq) and K2CO3 (2.64 g, 19.116 mmol, 3.0 eq) in acetone (50 ml) was stirred for 16 hours at boiling temperature. After monitoring by TLC, the mixture was concentrated, diluted with DCM (100 ml) and washed with water (50 ml) and sat. NaCl solution (50 ml). The org. phase was dried over sodium sulfate and concentrated under reduced pressure, and the crude product so obtained was purified by column chromatography (silica gel, 2% MeOH in DCM). Yield: 49% (1.3 g, 3.14 mmol)

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with DCM (100 ml)
  3. washwashed with water (50 ml) and sat. NaCl solution (50 ml)
  4. dry with materialphase was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3938d30a870406da1e91bf3d6648091
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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