Chloroform → Benzyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylate

HRID 1195661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195661
[C:1]1([CH2:7][O:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].ClC(Cl)Cl>O>[C:1]1([CH2:7][O:8][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][CH2:13]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 10012639Ethyl 3-piperidin-4-ylpropanoate

Produkt 1

HCID 14989191Benzyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 54 parts of (phenylmethyl)carbonochloridate, 60 parts of ethyl 4-piperidinepropanoate, 31.8 parts of sodium carbonate and 600 parts of trichloromethane was stirred overnight at room temperature. Water was added and the layers were separated. The organic layer was dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 71 parts (74%) of ethyl 1-(phenylmethoxycarbonyl)-4-piperidinepropanoate as a residue (interm. 1).

Aufarbeitung

  1. customthe layers were separated
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. filtrationThe residue was purified by filtration over silica gel using
  6. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-08ff2416e8c942d3a0575bc504629310
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112825

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