Hydrochloric Acid → 1,4'-Bipiperidin-4-ol

HRID 1293539

Reaktionsgleichung

Reaktionsgleichung von HRID 1293539
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=O)(C)(C)C.OC1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClC(Cl)C.CO.C(O)(=O)C>[N:8]1([CH:6]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 79341Piperidin-4-olHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 220613421,4'-Bipiperidin-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (20 g) and 4-hydroxypiperidine (6.7 g) were stirred together in dichloroethane (200 ml) with acetic acid (4 ml) at RT for 30 minutes. Sodium triacetoxyborohydride (23 g) was then added and the mixture stirred at RT overnight. The mixture was evaporated to dryness and the residue taken into water, extracted with diethyl ether (3×200 ml), the aqueous was basified to pH 9-10 and extracted with dichloromethane (3×200 ml). The dichloromethane extracts were combined, dried (MgSO4) and evaporated to leave an oil (19 g; same compound as Example 9 step 1). The oil was dissolved in methanol (300 ml) and treated with concentrated hydrochloric acid (5 ml). The mixture was stirred overnight and then evaporated to dryness to leave the title compound as the hydrochloride salt (15 g).

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. extractionextracted with diethyl ether (3×200 ml)
  3. extractionextracted with dichloromethane (3×200 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto leave an oil (19 g; same compound as Example 9 step 1)
  7. stirringThe mixture was stirred overnight
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8de0663424914a7d9132d897e1b9eb30
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238811B2

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