Acetic Anhydride → HCID 86682041, compound

HRID 1749914Notes

Reaction equation

HRID 1749914 reaction equation
[C:1]([C:4]1[C:5]([OH:28])=[C:6]([C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=1)[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)(=[O:3])[CH3:2].[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:29]([O:28][C:5]1[C:4]([C:1](=[O:3])[CH3:2])=[CH:23][C:22]([O:24][CH3:25])=[C:21]([O:26][CH3:27])[C:6]=1[CH2:7][N:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]1)(=[O:31])[CH3:30]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86682040HCID 86682040, compound

Product 1

HCID 86682041HCID 86682041, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of tert-butyl 4-(3-acetyl-2-hydroxy-5,6-dimethoxybenzyl)piperazine-1-carboxylate (0.20 g, 0.50 mmol) in pyridine (1.0 mL) was successively added with acetic anhydride (1.0 mL) and 4-dimethylaminopyridine (0.010 g), and the mixture was stirred at room temperature for 15 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 (2:1→3:7)) to obtain tert-butyl 4-(2-acetoxy-3-acetyl-5,6-dimethoxybenzyl)piperazine-1-carboxylate (0.15 g, 70%).

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 (2:1→3:7))

Sources & evidence

ORD record
ord-175eb7f7843a4f1ead099def718be9a6
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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