Dimethylformamide → 1-Tert-butyloxycarbonyl-4-[(4-pyrrolidinophenyloxy)methyl]piperidine

HRID 1079390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1079390
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Br[CH:35]([CH:37](Br)[CH3:38])[CH3:36]>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:38][CH2:37][CH2:35][CH2:36]3)=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 215082,3-DibromobutaneHCID 23366952Tert-butyl 4-((4-aminophenoxy)methyl)piperidine-1-carboxylate

Produkt 1

HCID 233669661-Tert-butyloxycarbonyl-4-[(4-pyrrolidinophenyloxy)methyl]piperidineAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 1-tert-butyloxycarbonyl-4-[(4-aminophenyloxy)methyl]piperidine (0.75 g) obtained in Example 13 were added dimethylformamide (10 ml), potassium carbonate (1.4 g) and dibromobutane (0.54 g) and the mixture was heated to 70° C. and stirred overnight. To the reaction solution was added water which was extracted with ethyl acetate (50 ml×3). The combined extract was dried over sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=5/1 (v/v)) to obtain 1-tert-butyloxycarbonyl-4-[(4-pyrrolidinophenyloxy)methyl]piperidine (0.55 g) as colorless crystals, m.p. 141°-145° C.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate (50 ml×3)
  2. extractionThe combined extract
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=5/1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-30fb7d061a3c46b98cb0c872aa1589f6
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05580883

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