Acetic Anhydride → HCID 86682044, compound

HRID 1749919Notes

Reaction equation

HRID 1749919 reaction equation
[C:1]([C:4]1[C:5]([OH:27])=[C:6]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:28]([O:27][C:5]1[C:4]([C:1](=[O:3])[CH3:2])=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[C:6]=1[CH2:13][N:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1)(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 71278847HCID 71278847, compound

Product 1

HCID 86682044HCID 86682044, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of tert-butyl 4-[(6-acetyl-5-hydroxybenzo[d][1,3]dioxol-4-yl)methyl]piperazine-1-carboxylate (0.18 g, 0.48 mmol) in pyridine (1.0 mL) was added with acetic anhydride (1.0 mL) and 4-dimethylaminopyridine (0.010 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with ice water, the mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (7:3→3:7)) to obtain tert-butyl 4-[(5-acetoxy-6-acetylbenzo[d][1,3]dioxol-4-yl)methyl]piperazine-1-carboxylate (0.18 g, 87%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (7:3→3:7))

Sources & evidence

ORD record
ord-b1b006239678487a89b37488b580534f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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