Water → racemic 2-(4-phenylphenyl)-2-(2-pyridyl)-4-[N,N-bis(1-methylethyl)amino]butanenitrile

HRID 638330

反応式

HRID 638330 の反応式
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:16][CH2:17][N:18]([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[C:14]#[N:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[K+].Br[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.O>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)([CH2:16][CH2:17][N:18]([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:20])[CH3:21])[C:14]#[N:15])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 962WaterHCID 79732-BromopyridineHCID 82127Potassium hydrideHCID 14569341alpha-(4-Biphenylyl)-alpha-[2-(diisopropylamino)ethyl]acetonitrile

生成物 1

HCID 13526571racemic 2-(4-phenylphenyl)-2-(2-pyridyl)-4-[N,N-bis(1-methylethyl)amino]butanenitrile収率 88.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A mixture of 50.0 g (0.16 mole) of 2-(4-phenylphenyl)-4-[N,N-bis(1-methylethyl)amino]butanenitrile and 29.7 g of potassium hydride (about 0.26 mole as a 35% dispersion in oil) in 1000 ml of toluene was heated at 65°. A solution of 32 g (0.20 mole) of 2-bromopyridine in 450 ml of toluene was added slowly. After addition was complete, the mixture was stirred an additional 30 minutes, cooled in an ice bath, and treated with 750 ml of water. The toluene layer was separated and extracted with 10% aqueous hydrochloric acid. The acidic aqueous layer was neutralized with a slight excess of aqueous sodium hydroxide and extracted wih dichloromethane. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness, giving 56.5 g of the title compound as an oil having the expected NMR spectrum. The intermediate nitrile was used without further purification.

後処理

  1. temperaturewas heated at 65°
  2. additionAfter addition
  3. temperaturecooled in an ice bath
  4. customThe toluene layer was separated
  5. extractionextracted with 10% aqueous hydrochloric acid
  6. extractionextracted wih dichloromethane
  7. washThe organic phase was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-a23e1afac98c4b6fb2a820f6ab684340
出典データセット
uspto-grants-1985_12
特許番号
US04560754

関連ノート

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