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

HRID 1900085노트

반응식

HRID 1900085 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-f9830ce84748488ea495eb73b0c0a207
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574055

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