Pyridine → (RS)-1-acetyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine

HRID 1900065Notes

Reaction equation

HRID 1900065 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5]1.[C:22](OC(=O)C)(=[O:24])[CH3:23].N1C=CC=CC=1>C(Cl)Cl>[C:22]([N:19]1[CH2:20][CH2:21][CH:16]([C:13]2[CH:12]=[CH:11][C:10]([N:6]3[CH2:5][CH:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[CH:15][CH:14]=2)[CH2:17][CH2:18]1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 23371817(RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine

Product 1

HCID 23371884(RS)-1-acetyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidineYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

177.1 mg (0.61 mmol) of (RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine were dissolved in 20 ml of methylene chloride and treated with 68.5 mg (0.67 mmol) of acetic anhydride in the presence of 53.1 mg (0.67 mmol) of pyridine. After stirring at room temperature for 18 hours the mixture was washed with water and the organic phase was dried over sodium sulfate. After filtration and evaporation of the filtrate the product was dried in a high vacuum. 197.3 mg of (RS)-1-acetyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine were obtained as a yellowish oil. 1H-NMR (CDCl3) ppm: 7.49 (d,2H), 7.20 (d,2H), 4.80 (m,2H), 4.05 (t, 1H), 3.92 (m,2H), 3.64 (d,2H), 3.43 (s,3H), 3.21 (m,1H), 2.68 (m,2H), 2.14 (s,3H), 1.85 (m,2H), 1.60 (m,2H).

Workup

  1. washwas washed with water
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. filtrationAfter filtration and evaporation of the filtrate the product
  4. customwas dried in a high vacuum

Sources & evidence

ORD record
ord-3cfdfae420114e2e82e978e247292b6a
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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