Ammonia → (RS)-2-Amino-2-(4-chloro-phenyl)-butyronitrile

HRID 1911561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911561
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.[NH3:12].C[Si]([C:17]#[N:18])(C)C>CO.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[NH2:12][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([CH2:9][CH3:10])[C:17]#[N:18]

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 226974'-ChloropropiophenoneHCID 82115Trimethylsilyl cyanide

Produkt 1

HCID 16783758(RS)-2-Amino-2-(4-chloro-phenyl)-butyronitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 4′-chloropropiophenone (5 g) in MeOH (20 ml) was treated under an argon atmosphere and at r.t. with 7M NH3 in MeOH (33.9 ml). Then, tetraisopropyl orthotitanate (10.54 ml) was added dropwise. The reaction mixture was stirred for 1 hr at r.t. Then, trimethylsilyl cyanide (3.72 ml) was added and stirring was continued at r.t. overnight. The reaction mixture was poured in ice and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The crude (RS)-2-amino-2-(4-chloro-phenyl)-butyronitrile (4.95 g) was used in the next reaction step without further purification.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at r.t. overnight
  3. additionThe reaction mixture was poured in ice
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude (RS)-2-amino-2-(4-chloro-phenyl)-butyronitrile (4.95 g) was used in the next reaction step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-1c663d5fdc7542d2b068d7e1eed39484
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604061B2

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