Water → HCID 68299252, compound

HRID 1844676Notes

Reaction equation

HRID 1844676 reaction equation
[NH2:1][CH:2]([CH:5]1[CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]1)[C:3]#[N:4].CCN(CC)CC.[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:22]=1[CH2:29][C:30](Cl)=[O:31].O>C1COCC1>[C:3]([CH:2]([CH:5]1[CH2:6][CH2:7][N:8]([O:11][CH3:12])[CH2:9][CH2:10]1)[NH:1][C:30](=[O:31])[CH2:29][C:22]1[C:21]([CH3:20])=[CH:26][C:25]([CH3:27])=[CH:24][C:23]=1[CH3:28])#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 110307542,4,6-Trimethylbenzeneacetyl chlorideHCID 68299240HCID 68299240, compound

Product 1

HCID 68299252HCID 68299252, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of amino-(1-methoxy-piperidin-4-yl)-acetonitrile (500 mg, 2.95 mmol) and Et3N (610 mg, 6.02 mmol) in THF (15 ml), was added (2,4,6-trimethyl-phenyl)-acetyl chloride (581 mg, 2.95 mmol). After the addition, the mixture was stirred at room temperature for 0.5 h. Then, the mixture was poured into water (100 ml) and extracted with CH2Cl2 (3×50 ml). The combined organic layers were dried over Na2SO4, filtered and evaporated under vacuum. The residue was purified by chromatography on silica gel. Yield: 700 mg of N-[cyano-(1-methoxy-piperidin-4-yl)-methyl]-2-(2,4,6-trimethyl-phenyl)-acetamide as a solid.

Workup

  1. additionAfter the addition
  2. extractionextracted with CH2Cl2 (3×50 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-62618a20f2dd46a28c77a46f55dc1d06
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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