Acetic Anhydride → 4-Acetoxy-1-benzyl-3,5-dimethylpiperidine

HRID 396309Notes

Reaction equation

HRID 396309 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]([CH3:14])[CH:11]([OH:15])[CH:10]([CH3:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:17]([O:15][CH:11]1[CH:12]([CH3:14])[CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH:10]1[CH3:16])(=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 230036661-Benzyl-3,5-dimethylpiperidin-4-ol

Product 1

HCID 230036764-Acetoxy-1-benzyl-3,5-dimethylpiperidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N-benzyl-4-hydroxy-3,5-dimethylpiperidine (21.9 g, 0.1 mole), acetic anhydride (15.3 g), N,N-dimethyl-4-aminopyridine (0.01 g) and pyridine (100 ml) was stirred at 110° C. for 2 hr. The reaction mixture was concentrated to dryness, triturated with water (50 ml) and extracted with chloroform (2×50 ml). The extract was dried (Na2SO4) and concentrated to dryness to furnish a crude mixture of cis- and trans-4-acetoxy-1-benzyl-3,5-dimethylpiperidine. Yield 16 g (61.3%), C16H23NO2, m/z 262 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (50 ml)
  3. extractionextracted with chloroform (2×50 ml)
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated to dryness
  6. customto furnish a crude

Sources & evidence

ORD record
ord-388b92eb2d664329a5407b754b747b07
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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