Ethanolamine → N-(2-hydroxyethyl)-4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzamide

HRID 484497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 484497
[OH:1][C:2]1([CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[NH2:27][CH2:28][CH2:29][OH:30]>O>[OH:30][CH2:29][CH2:28][NH:27][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][C:2]2([OH:1])[CH2:3][CH2:4][N:5]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:6][CH2:7]2)=[CH:26][CH:25]=1

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 222912651-Benzyl-4-(4-methoxycarbonylphenoxymethyl)piperidin-4-ol

Produkt 1

HCID 14989215N-(2-hydroxyethyl)-4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzamideAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A mixture of 10.7 parts of methyl 4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzoate and 8 parts of 2-aminoethanol was stirred for 4 hours in an oil bath at 145° C. After cooling, the reaction mixture was poured into water. The oil was decanted, washed twice with water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of 2,2-oxybispropane and 2-propanol. The product was filtered off and dried yielding 8 parts (69.3%) of N-(2-hydroxyethyl)-4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzamide; mp. 161.1° C. (int. 80).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe oil was decanted
  3. washwashed twice with water
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from a mixture of 2,2-oxybispropane and 2-propanol
  9. filtrationThe product was filtered off
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ebbcc386b9ad4cbc91224d23dbe196af
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05231184

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