Water → N-p-Benzeneacetonitrile menthanecarboxamide

HRID 1970193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970193
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[C:11]([NH2:13])=[O:12])([CH3:3])[CH3:2].[C:14]([CH2:16][C:17]1[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=1)#[N:15].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O.CNCCNC>[Cu]I.C1(C)C=CC=CC=1>[C:14]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:13][C:11]([C@@H:5]2[CH2:6][C@H:7]([CH3:10])[CH2:8][CH2:9][C@H:4]2[CH:1]([CH3:2])[CH3:3])=[O:12])=[CH:19][CH:18]=1)#[N:15]

Komponenten

8

Edukt 5

HCID 962WaterHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 1428664-IodophenylacetonitrileHCID 59253413(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexane-1-carboxamide

Produkt 1

HCID 44467796N-p-Benzeneacetonitrile menthanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 250 mL 3-neck flask was fitted with a condenser and a nitrogen inlet was charged with 10.00 g (0.0546 mol) of (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide, 0.522 g (0.0027 mol) copper (I) iodide, 13.26 g (0.0546 mol) of 4-(cyanomethyl)phenyl iodide, 23.18 g (0.109 mol) of potassium phosphate. The system was purged with nitrogen and a magnetic stir bar was added. After the addition of 170 mL of toluene, 3.42 g (0.190 mol) of water and 0.964 g (0.0109 mol) of N,N′-dimethylethylene diamine, the mixture was heated to 100° C. and stirred for 21 h under nitrogen. The crude reaction mixture was filtered through 50 g of silica gel (wet with 1:1 ethyl acetate/methylene chloride), and the bed was rinsed three times with 1:1 ethyl acetate/methylene chloride (150+75+75 mL). Concentration of the mixture in vacuo provided N-[4-(cyanomethyl)phenyl]-(1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide as a thick oil oil which was further purified by flash chromatography on silica gel eluting with mixtures of ethyl acetate and hexanes. The product has the following properties with the structure confirmed by obtaining an X-ray crystal structure of a sample crystallized from hexane/ethyl acetate.

Aufarbeitung

  1. customA 250 mL 3-neck flask was fitted with a condenser and a nitrogen inlet
  2. customThe system was purged with nitrogen and a magnetic stir bar
  3. additionwas added
  4. customThe crude reaction mixture
  5. filtrationwas filtered through 50 g of silica gel (wet with 1:1 ethyl acetate/methylene chloride)
  6. washthe bed was rinsed three times with 1:1 ethyl acetate/methylene chloride (150+75+75 mL)

Quellen und Nachweise

ORD-Eintrag
ord-132e5c42d9064b3cba9203bd53abc619
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426643B2

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