Acetic Acid → Tert-butyl 4-[(3-chlorophenyl)methyl]piperazine-1-carboxylate

HRID 1783325

Reaktionsgleichung

Reaktionsgleichung von HRID 1783325
[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:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClC(Cl)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([Cl:14])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 114773-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 4316940Tert-butyl 4-[(3-chlorophenyl)methyl]piperazine-1-carboxylateAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of piperazine-1-carboxylic acid tert-butyl ester (4.00 g, 21.5 mmol) in dry dichloroethane (70 mL) are added 3-chlorobenzaldehyde (2.49 mL, 3.08 g, 21.9 mmol), HOAc (2.58 mL, 2.71 g, 45.1 mmol) and NaBH(OAc)3 (5.46 g, 25.8 mmol) at ambient temperature. After stirring at ambient temperature for 3d, 2N NaOH (40 mL) is added, the layers are separated, and the aqueous layer is extracted with CH2Cl2 (4×50 mL). The combined organic extracts are washed with water (3×50 mL) and brine (80 mL) and dried over MgSO4. The crude material is purified by chromatography on silica gel, eluting with hexane:EtOAc mixtures, yielding 5.83 g (18.8 mmol, 87%) of the title compound as yellow oil. MS (ES): m/z 311.0/313.0 (50/18) [MH+]. tR (method A)=5.0 min.

Aufarbeitung

  1. additionis added
  2. customthe layers are separated
  3. extractionthe aqueous layer is extracted with CH2Cl2 (4×50 mL)
  4. washThe combined organic extracts are washed with water (3×50 mL) and brine (80 mL)
  5. dry with materialdried over MgSO4
  6. customThe crude material is purified by chromatography on silica gel
  7. washeluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-5a0e1ba5626842d9a0e913e15b5f3977
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501407B2

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