Triethylamine → cis-1-[4-[3-Methoxy-4-[(phenylmethyl)amino]-1-piperidinyl]-1-oxobutyl]pyrrolidine

HRID 2248623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2248623
Cl[CH2:2][CH2:3][CH2:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].[CH3:12][O:13][C@H:14]1[C@@H:19]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17][NH:16][CH2:15]1.C(N(CC)CC)C>CN(C)C=O>[CH3:12][O:13][C@H:14]1[C@@H:19]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17][N:16]([CH2:2][CH2:3][CH2:4][C:5]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:6])[CH2:15]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3040794-Chloro-1-(pyrrolidin-1-yl)butan-1-one2×HCID 13677805cis-3-methoxy-N-(phenylmethyl)-4-piperidinamine

Produkt 1

HCID 70048899cis-1-[4-[3-Methoxy-4-[(phenylmethyl)amino]-1-piperidinyl]-1-oxobutyl]pyrrolidineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 43.9 parts of 1-(4-chloro-1-oxobutyl)pyrrolidine, 55.1 parts of cis-3-methoxy-N-(phenylmethyl)-4-piperidinamine, 37.8 parts of N,N-diethylethanamine and 900 parts of N,N-dimethylformamide was stirred overnight at 70° C. Another portion of 4.4 parts of 1(4-chloro-1-oxobutyl)pyrrolidine was added and stirring was continued overnight at 70° C. The reaction mixture was evaporated and the residue was taken up in a mixture of water and sodium carbonate. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 53.1 parts (59.0%) of cis-1-[4-[3-methoxy-4-[(phenylmethyl)amino]-1-piperidinyl]-1-oxobutyl]pyrrolidine as a residue (int. 42).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued overnight at 70° C
  3. customThe reaction mixture was evaporated
  4. additionthe residue was taken up in a mixture of water and sodium carbonate
  5. extractionThe product was extracted with dichloromethane
  6. washThe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-764e0798fcb9449691bdf3ac3b3bacb9
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05041454

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