Chloroacetamide → HCID 59854945, compound

HRID 2375364Notes

Reaction equation

HRID 2375364 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:4]([NH2:6])=[S:5])#[N:2].[C:13]([N:20]1[CH2:25][CH2:24][CH2:23][C:22](=O)[CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].N1CCOCC1.Cl[CH2:34][C:35]([NH2:37])=[O:36].C([O-])([O-])=O.[K+].[K+]>C(O)C>[C:16]([O:15][C:13]([N:20]1[CH2:25][C:24]2[N:6]=[C:4]3[S:5][C:34]([C:35](=[O:36])[NH2:37])=[C:1]([NH2:2])[C:3]3=[C:7]([C:8]3[S:9][CH:10]=[CH:11][CH:12]=3)[C:23]=2[CH2:22][CH2:21]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 5

HCID 6580ChloroacetamideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 27298552-Cyano-3-thiophen-2-yl-thioacrylamideHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Product 1

HCID 59854945HCID 59854945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-cyano-3-thiophen-2-yl-thioacrylamide (4.38 g, 22.5 mmol) and 1-boc-3-piperidone (4.49 g, 22.5 mmol) in 200 ml of anhydrous ethanol was added morpholine (3.94 g, 45 mmol) at room temperature with stirring. The resulting mixture was heated to reflux overnight. Then, 2-chloroacetamide (4.21 g, 45 mmol) and K2CO3 (6.23 g, 45 mmol) was added. The reaction mixture was continued to heat at 80° C. overnight. The solvent was removed in vacuo, and the residue was purified by silica gel column (chloroform/methanol, 40:1) and recrystallized from methanol to give a yellow crystalline product.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel column (chloroform/methanol, 40:1)
  5. customrecrystallized from methanol
  6. customto give a yellow crystalline product

Sources & evidence

ORD record
ord-70b651da65ca436a89d231c1513c60d7
Source dataset
uspto-grants-2008_12
Patent number
US07465742B2

Reaction notes

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