Potassium Carbonate → N-(4-cyano-1-ethoxy-piperidin-4-yl)-2-(2,4,6-trimethyl-phenyl)-acetamide

HRID 1962363

Reaction equation

HRID 1962363 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 59614586N-(4-cyano-1-ethoxy-piperidin-4-yl)-2-(2,4,6-trimethyl-phenyl)-acetamideYield 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 were 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 was poured into 100 ml of ice water and extracted with ethyl acetate. The organic phase was 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.

Workup

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

Sources & evidence

ORD record
ord-2cf93ac1b11c47c39308d7baaf7c629b
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Linked notes

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