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Hydrochloric Acid → cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[4-(methylamino)butyl]-4-piperidinyl]benzamide

HRID 1165037
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1165037
[NH2:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:19](C)[C:20](=O)OC(C)(C)C)[CH2:11][C@H:10]2[O:28][CH3:29])=[O:7])=[C:4]([O:33][CH3:34])[CH:3]=1.Cl>CC(O)C>[NH2:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH3:20])[CH2:11][C@H:10]2[O:28][CH3:29])=[O:7])=[C:4]([O:33][CH3:34])[CH:3]=1
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67922785(1,1-Dimethylethyl) cis-[4-[4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-3-methoxy-1-piperidinyl]butyl]methylcarbamate

Produkt 1

HCID 14854963cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[4-(methylamino)butyl]-4-piperidinyl]benzamideAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of (1,1-dimethylethyl) cis-[4-[4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-3-methoxy-1-piperidinyl]butyl]methylcarbamate and 250 parts of 2-propanol, saturated with hydrochloric acid was stirred and refluxed for 15 minutes. The reaction mixture was evaporated and the residue was taken up in trichloromethane. The organic layer was washed with water, saturated with ammonium hydroxide, 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. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 33 parts (78.7%) of cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[4-(methylamino)butyl]-4-piperidinyl]benzamide; mp. 129.3° C. (interm. 9).

Aufarbeitung

  1. temperaturerefluxed for 15 minutes
  2. customThe reaction mixture was evaporated
  3. washThe organic layer was washed with water, saturated with ammonium hydroxide
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from acetonitrile
  12. filtrationThe product was filtered off
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0c993dd33c904aa2b79ab064e06c236b
Quelldatensatz
uspto-grants-1990_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04906643

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