Acetic Anhydride → HCID 67447123, compound

HRID 2368082Notes

Reaction equation

HRID 2368082 reaction equation
[NH2:1][CH:2]([CH3:18])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(OCC)(=O)C>[C:19]([NH:1][CH:2]([CH3:18])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 575174851344684-60-1

Product 1

HCID 67447123HCID 67447123, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 4-(3-aminobutyl)piperidine-1-carboxylate (3.58 g) and acetic anhydride (4.13 g) in ethyl acetate (100 mL) was heated under reflux for 3 hr. The reaction mixture was allowed to cool to room temperature, washed with aqueous citric acid solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.65 g).

Workup

  1. temperatureunder reflux for 3 hr
  2. washwashed with aqueous citric acid solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4c3c77ae453046f5aca65df0ecc565ba
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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