Hydrochloric Acid → 3-(1-Benzyl-piperidin-4-ylamino)-propan-1-ol

HRID 1167588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167588
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[OH-].[Na+]>C(Cl)Cl>[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 90863-Amino-1-propanolHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 31534663-(1-Benzyl-piperidin-4-ylamino)-propan-1-olAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

16.5 g of 3-aminopropanol and 41.7 g of 1-benzyl-4-piperidone are dissolved in 350 ml methylene chloride and at about 10° C. 56 g of sodium triacetoxy-borohydride are slowly added. The mixture is stirred overnight at ambient temperature, then acidified with dilute hydrochloric acid with cooling and subsequently made alkaline with conc. sodium hydroxide solution. The organic phase is separated off, the aqueous phase is washed once again with 150 ml of methylene chloride. The combined organic phases are dried over sodium sulphate and freed from solvent in vacuo. 32 g 1-benzyl-4-(3-hydroxy-propylamino)-piperidine are obtained as a yellow oil which is used in the next reaction step without any further purification.

Aufarbeitung

  1. temperaturewith cooling
  2. customThe organic phase is separated off
  3. washthe aqueous phase is washed once again with 150 ml of methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulphate

Quellen und Nachweise

ORD-Eintrag
ord-358fd5966c174100b04c06c091c75c3b
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620438B2

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