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

HRID 1900085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900085
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 23371871t-Butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylateAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f9830ce84748488ea495eb73b0c0a207
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05574055

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