4-Cyanobenzaldehyde → HCID 46869800, Verbindung

HRID 882335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882335
Cl.[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)#[N:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH:11][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 660424-CyanobenzaldehydeHCID 2723716Tranylcypromine hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 46869800HCID 46869800, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (trans)-2-phenylcyclopropanamine hydrochloride (0.25 g, 1.50 mmol) and 4-cyanobenzaldehyde (0.22 g, 1.65 mmol) in CH2Cl2 (8 mL) and water (0.5 mL) was vigorously stirred at room temperature for 10 min. Then, NaBH(OAc)3 (0.41 g, 1.95 mmol) was slowly added and stirring continued for 1.5 h. The reaction mixture was washed with an aqueous saturated solution of NaHCO3 (10 mL), the organic layer was dried over anhydrous Na2SO4, filtered and, after removal of the solvent, the residual oil was purified by column chromatography on silica gel (1% MeOH/CH2Cl2) affording 0.07 g of 4-({[(trans)-2-phenylcyclopropyl]amino}methyl)benzonitrile [Rf=0.6 (5% MeOH/CH2Cl2), colorless oil, 19% yield].

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 1.5 h
  3. washThe reaction mixture was washed with an aqueous saturated solution of NaHCO3 (10 mL)
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customafter removal of the solvent
  7. customthe residual oil was purified by column chromatography on silica gel (1% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e811af39cc6b43f8a860b3b77b10df35
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993808B2

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