Sodium Hydroxide → 4-(1-Benzylpiperidin-3-yl)piperazine-1-carboxylic acid tert-butyl ester

HRID 499224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499224
[OH-].[Na+].O.Cl.[CH2:5]([N:12]1[CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.ClCCCl>[C:22]([O:21][C:19]([N:26]1[CH2:31][CH2:30][N:29]([CH:14]2[CH2:15][CH2:16][CH2:17][N:12]([CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:13]2)[CH2:28][CH2:27]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27608961-Benzylpiperidin-3-one hydrochloride hydrateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 684554544-(1-Benzylpiperidin-3-yl)piperazine-1-carboxylic acid tert-butyl esterAusbeute 126,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

20 ml of a 10% sodium hydroxide solution are added to a suspension of 9.96 g of 1-benzyl-3-piperidone monohydrochloride hydrate in suspension in 200 ml of DCM. The medium is stirred, and the organic phase is separated by settling out and then washed with a saturated NaCl solution. After drying over MgSO4, the organic phase is concentrated. The gum obtained is taken up in 180 ml of DCE, 10.1 g of Boc-piperazine and then 15.9 g of NaBH(OAc)3 are added and the medium is stirred at AT for 12 h. The medium is concentrated and then taken up in EtOAc. The organic phase is washed twice with a saturated NaHCO3 solution, and then with a saturated NaCl solution. After drying over MgSO4, the organic phase is concentrated, to give 18.63 g of the expected product.

Aufarbeitung

  1. customthe organic phase is separated
  2. washwashed with a saturated NaCl solution
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic phase is concentrated
  5. customThe gum obtained
  6. stirringthe medium is stirred at AT for 12 h
  7. concentrationThe medium is concentrated
  8. washThe organic phase is washed twice with a saturated NaHCO3 solution
  9. dry with materialAfter drying over MgSO4
  10. concentrationthe organic phase is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-87910c87bace45b09c20b3724529269b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767681B2

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