Water → N-p-Benzeneacetonitrile menthanecarboxamide

HRID 407529ノート

反応式

HRID 407529 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

HCID 44467796N-p-Benzeneacetonitrile menthanecarboxamide

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-10b88ddd19f54e7a92c349a6791c2a5f
出典データセット
uspto-grants-2014_06
特許番号
US08754259B2

反応ノート

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