Potassium Carbonate → HCID 68299234, compound

HRID 1844665Notes

Reaction equation

HRID 1844665 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].[NH2:14][CH:15]([CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([O:25][CH3:26])[CH2:21][CH2:20]1)[C:16]#[N:17].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[C:16]([CH:15]([NH:14][C:11](=[O:12])[CH2:10][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=1[CH3:9])[CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([O:25][CH3:26])[CH2:21][CH2:20]1)#[N:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110307542,4,6-Trimethylbenzeneacetyl chlorideHCID 68299265HCID 68299265, compound

Product 1

HCID 68299234HCID 68299234, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, (2,4,6-trimethyl-phenyl)-acetyl chloride (10.6 g, 54 mmol) was added dropwise to a mixture of 2-amino-3-(1-methoxy-piperidin-4-yl)-propionitrile (6.6 g, 36 mmol) and K2CO3 (9.9 g, 72 mmol) in 100 ml of THF. After the addition, the mixture was stirred for 0.5 h. The reaction mixture was diluted with 50 ml of water and extracted with EtOAc five times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography on silica gel Yield: 10.6 g of N-[1-cyano-2-(1-methoxy-piperidin-4-yl)-ethyl]-2-(2,4,6-trimethyl-phenyl)-acetamide as a solid.

Workup

  1. additionAfter the addition
  2. extractionextracted with EtOAc five times
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography on silica gel Yield: 10.6 g of N-[1-cyano-2-(1-methoxy-piperidin-4-yl)-ethyl]-2-(2,4,6-trimethyl-phenyl)-acetamide as a solid

Sources & evidence

ORD record
ord-d68261d522a74c769990d2058c09def1
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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