Pyridine → t-Butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate

HRID 1900085ノート

反応式

HRID 1900085 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23].N1C=CC=CC=1>C(Cl)Cl>[CH2:25]([O:24][C:22]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1)=[O:23])[CH3:26]

参加物

5

反応物 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

生成物 1

HCID 23371871t-Butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate収率 55.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

8.84 g (32.0 mmol) of t-butyl 4-(4-aminophenyl)-piperidine-1-carboxylate were dissolved in 150ml of methylene chloride and treated with 3.82 g (35.2 mmol) of ethyl chloroformate in the presence of 2.78 g (35.2 mmol) of pyridine. The reaction mixture was stirred at room temperature for 16 hours. Thereafter, it was washed with water and the organic phase was dried over sodium sulfate, filtered and evaporated. The residue (11.3 g) was chromatographed on 95 g of silica gel 60 with ether/n-hexane (4:6). After recrystallization from ether/n-hexane there were obtained 6.15 g of t-butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate. M.p.: 126°-128°.

後処理

  1. washThereafter, it was washed with water
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue (11.3 g) was chromatographed on 95 g of silica gel 60 with ether/n-hexane (4:6)
  6. customAfter recrystallization from ether/n-hexane there

出典と根拠

ORDレコード
ord-f9830ce84748488ea495eb73b0c0a207
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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