Benzyl Bromide → (RS)-1-benzyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine

HRID 1900064Notes

Reaction equation

HRID 1900064 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.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:22]([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)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 23371817(RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine

Product 1

HCID 23371820(RS)-1-benzyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidineYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

290.4 mg (1.0 mmol) of (RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine were dissolved in 5 ml of abs. dimethylformamide and treated with 171.0 mg(1.0 mmol) of benzyl bromide in the presence of 404.8 mg (4.0 mmol) of triethylamine. The reaction mixture was stirred at 600 for 90 minutes. Thereafter, it was evaporated, the residue was partitioned in ethyl acetate and 3N ammonia solution and the organic phase was washed with water, dried over sodium sulfate, filtered and evaporated. The base was dissolved in ethanol, made acid with ethereal hydrochloric acid and distilled repeatedly with toluene. After recrystallization from ethanol/ether there were obtained 291.2 mg of (RS)-1-benzyl-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine.HCl. M.p.: 175°-177°.

Workup

  1. customThereafter, it was evaporated
  2. customthe residue was partitioned in ethyl acetate
  3. wash3N ammonia solution and the organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe base was dissolved in ethanol
  8. distillationdistilled repeatedly with toluene
  9. customAfter recrystallization from ethanol/ether there

Sources & evidence

ORD record
ord-be32cebe1995486798208b7965de51b7
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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