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

HRID 1900064ノート

反応式

HRID 1900064 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-be32cebe1995486798208b7965de51b7
出典データセット
uspto-grants-1996_11
特許番号
US05574055

反応ノート

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