Potassium Carbonate → HCID 59614586, compound

HRID 1022375

Reaction equation

HRID 1022375 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:10][C:11](Cl)=[O:12].C(=O)([O-])[O-].[K+].[K+].[NH2:20][C:21]1([C:30]#[N:31])[CH2:26][CH2:25][N:24]([O:27][CH2:28][CH3:29])[CH2:23][CH2:22]1>C(#N)C>[C:30]([C:21]1([NH:20][C:11](=[O:12])[CH2:10][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=2[CH3:9])[CH2:26][CH2:25][N:24]([O:27][CH2:28][CH3:29])[CH2:23][CH2:22]1)#[N:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110307542,4,6-Trimethylbenzeneacetyl chlorideHCID 59614603HCID 59614603, compound

Product 1

HCID 59614586HCID 59614586, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3.0 g of (2,4,6-trimethyl-phenyl)-acetyl chloride and 10 g of potassium carbonate in 90 ml of acetonitrile are treated at 0° C. with a solution of 3.6 g of 4-amino-1-ethoxy-piperidine-4-carbonitrile in 30 ml of acetonitrile. After stirring for 18 hours at room temperature the reaction mixture is poured into 100 ml of ice water and extracted with ethyl acetate. The organic phase is washed with brine and concentrated. Chromatography (heptane/ethyl acetate 5:1) yielded 4.5 g of N-(4-cyano-1-ethoxy-piperidin-4-yl)-2-(2,4,6-trimethyl-phenyl)-acetamide as a solid, mp: 194-195° C. LC-MS (EI, ES+): 330 (M+H)+

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bb5550c20e8d40b18b67a2d2f36fc7b7
Source dataset
uspto-grants-2014_05
Patent number
US08722578B2

Linked notes

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