Potassium Carbonate → Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(ethyl)carbamate

HRID 1193415Notes

Reaction equation

HRID 1193415 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:10]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:9].Cl[C:28]1[CH:33]=[C:32]([CH3:34])[N:31]=[C:30]([CH3:35])[N:29]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:35][C:30]1[N:29]=[C:28]([N:24]2[CH2:25][CH2:26][CH:21]([N:10]([CH2:8][CH3:9])[C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:22][CH2:23]2)[CH:33]=[C:32]([CH3:34])[N:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31541994-Chloro-2,6-dimethylpyrimidineHCID 66799319Benzyl ethyl(piperidin-4-yl)carbamate trifluoroacetate

Product 1

HCID 66798660Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(ethyl)carbamateYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of benzyl ethyl(piperidin-4-yl)carbamate trifluoroacetate (4.14 mmol, 1.0 eq), 4-chloro-2,6-dimethylpyrimidine (0.706 g, 4.97 mmol, 1.2 eq) and K2CO3 (1.14 g, 8.28 mmol, 2.0 eq) in acetone (20 ml) was stirred for 14 hours at boiling temperature. After monitoring by TLC, the mixture was concentrated, diluted with DCM (200 ml), washed with water (80 ml) and sat. NaCl solution (80 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 2.0% MeOH in DCM). Yield: 63% (960 mg, 2.60 mmol)

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with DCM (200 ml)
  3. washwashed with water (80 ml) and sat. NaCl solution (80 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, 2.0% MeOH in DCM)

Sources & evidence

ORD record
ord-66f53c3388e9491199943c5b5d2ca2b8
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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