Acetic Anhydride → HCID 54131508, compound

HRID 1003387Notes

Reaction equation

HRID 1003387 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[CH:5][CH:4](CO)[CH2:3]1.[C:10]([O:13]C(=O)C)(=[O:12])[CH3:11]>C(N(CC)CC)C>[C:10]([O:13][CH:4]1[CH:5]=[CH:6][CH2:7][N:2]([CH3:1])[CH2:3]1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15015382HCID 15015382, compound

Product 1

HCID 54131508HCID 54131508, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of (1-methyl-1,2,3,6-tetrahydro-3-pyridyl)methanol (0.7 g, 5.5 mmol), triethylamine (25 ml), and acetic anhydride (20 ml) was refluxed for 2h. The reaction mixture was extracted with methylene chloride and pH was adjusted to 10 with aqueous sodium hydroxide. The solution was extracted with methylene chloride, which was dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was purified on a silica gel column (Eluent: methanol/methylene chloride (1/9)) to give 1-methyl-1,2,3,6-tetrahydropyridin-3-yl acetate as an oil (Yield: 0.69 9, 70%).

Workup

  1. extractionThe reaction mixture was extracted with methylene chloride and pH
  2. extractionThe solution was extracted with methylene chloride, which
  3. dry with materialwas dried over magnesium sulfate
  4. customevaporated to dryness in vacuo
  5. customThe residue was purified on a silica gel column (Eluent: methanol/methylene chloride (1/9))

Sources & evidence

ORD record
ord-571c5ce07bba4a96b7a63c677d559ec5
Source dataset
uspto-grants-2000_04
Patent number
US06046214

Reaction notes

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