Potassium Hydroxide → 4-[3-(4-Chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 331117

Reaktionsgleichung

Reaktionsgleichung von HRID 331117
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[CH:23]=O)=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[K+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([O:19][C:18]3[CH:28]=[CH:29][C:15]([Cl:14])=[CH:16][CH:17]=3)[CH:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 14797Potassium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6160153-(4-Chlorophenoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 674135414-[3-(4-Chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of piperazine-1-carboxylic acid tert-butyl ester (19.6 g, 105 mmol) and 3-(4-chloro-phenoxy)-benzaldehyde (24.4 g, 105 mmol) in THF (90 mL) was treated with NaB(OAc)3H (33.4 g, 158 mmol). After 3 h, the resulting mixture was treated with 10% aq. KOH (500 mL). The aqueous phase was extracted with EtOAc (2×500 mL) then saturated aqueous NaCl (200 mL). The organic extracts were combined, dried (MgSO4) and purified (FCC) to give 4-[3-(4-chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester (29.6 g, 75%). MS (ESI+): calcd for C22H27ClN2O3 m/z 402.17, found 403.2 (M+H)+.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with EtOAc (2×500 mL)
  2. dry with materialdried (MgSO4)
  3. custompurified (FCC)

Quellen und Nachweise

ORD-Eintrag
ord-3263a016ae2a4704b1a099e6813fb1c3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877769B2

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