Potassium Hydroxide → 4-(3,4-Dibromo-benzyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 40578

Reaktionsgleichung

Reaktionsgleichung von HRID 40578
[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].[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Br:23])[CH:18]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[K+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:18][C:17]2[CH:20]=[CH:21][C:22]([Br:23])=[C:15]([Br:14])[CH:16]=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 6220533,4-DibromobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 578808894-(3,4-Dibromo-benzyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of piperazine-1-carboxylic acid tert-butyl ester (3.5 g) and 3,4-dibromobenzaldehyde (5.0 g) in DCM (80 mL) was treated with NaB(OAc)3H (5.6 g). After 16 h, the resulting mixture was treated with 10% aq. KOH (80 mL). The aqueous phase was extracted with DCM (1×80 mL). The organic extracts were combined and dried (MgSO4). Most of the solvent was removed by concentration. Upon standing overnight, the resulting mixture produced crystals that were filtered and washed with DCM (1×5 mL), giving the title compound as a white crystalline solid (6.0 g).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with DCM (1×80 mL)
  2. dry with materialdried (MgSO4)
  3. customMost of the solvent was removed by concentration
  4. waitUpon standing overnight
  5. customthe resulting mixture produced crystals that
  6. filtrationwere filtered
  7. washwashed with DCM (1×5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-59d2975d85a348a1993e3f7f99008638
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530476B2

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