Acetyl chloride → 1-Acetyl-piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide

HRID 1020049Notes

Reaction equation

HRID 1020049 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[CH:11]=1)[CH3:2].CCN(CC)CC.[C:32](Cl)(=[O:34])[CH3:33]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([CH:19]2[CH2:24][CH2:23][N:22]([C:32](=[O:34])[CH3:33])[CH2:21][CH2:20]2)=[O:18])[CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59508999Piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide

Product 1

HCID 595090051-Acetyl-piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amideYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #1A) (0.25 g, 0.76 mmol) and NEt3 (0.01 mL, 0.76 mmol) in THF (10 ml) was added acetyl chloride (0.053 ml, 0.76 mmol) at 0° C. The mixture was stirred at room temperature for 20 min, then the solvent was distilled off; the residue was dissolved in water and extracted with ethyl acetate (3×10 ml). The organic layers were separated, combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was triturated with dry diethyl ether and the solid was filtered off to obtain 1-acetyl-piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #13A) (0.208 g, 73%) as a white solid.

Workup

  1. distillationthe solvent was distilled off
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. customThe organic layers were separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting crude product was triturated with dry diethyl ether
  9. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-66bd2011e28f4f8bb7a6cb0e642c414c
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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