Hydrochloric Acid → 5-[(3-Trifluoromethylphenethyl)-methylamino]-2-(3,5-dimethoxyphenyl)-2-isopropylvaleronitrile

HRID 1073249ノート

反応式

HRID 1073249 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH:19]([CH3:21])[CH3:20])([CH2:14][CH2:15][CH2:16][NH:17][CH3:18])[C:12]#[N:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(C(C1C=C(OC)C=C(OC)C=1)C#N)(C)C.CC(NCCCCl)=O.[H-].[Na+].Cl.[F:49][C:50]([F:61])([F:60])[C:51]1[CH:52]=[C:53]([CH2:57][CH:58]=O)[CH:54]=[CH:55][CH:56]=1>[Pd].C1(C)C=CC=CC=1>[F:49][C:50]([F:61])([F:60])[C:51]1[CH:52]=[C:53]([CH:54]=[CH:55][CH:56]=1)[CH2:57][CH2:58][N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][C:11]([C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)([CH:19]([CH3:21])[CH3:20])[C:12]#[N:13]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 3361051N-(3-chloropropyl)acetamideHCID 14183624alpha-Isopropyl-3,5-dimethoxyphenylacetonitrileHCID 212463392-(3-(Trifluoromethyl)phenyl)acetaldehydeHCID 221584772-(3,5-Dimethoxyphenyl)-2-isopropyl-5-methylaminovaleronitrile

生成物 1

HCID 139233825-[(3-Trifluoromethylphenethyl)-methylamino]-2-(3,5-dimethoxyphenyl)-2-isopropylvaleronitrile収率 86.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 1140Toluene溶媒

実験手順

A mixture of 29.0 g (0.1 mole) of 2-(3,5-dimethoxyphenyl)-2-isopropyl-5-methylaminovaleronitrile (prepared by reacting α-isopropyl-3,5-dimethoxyphenylacetonitrile and 3-methylformamido-1-chloropropane in the presence of sodium hydride and then eliminating the formyl group by means of hydrochloric acid) and 18.8 g (0.1 mole) of 3-trifluoromethylphenylacetaldehyde was reduced catalytically with 400 mg of 5% strength palladium on carbon in 100 ml of toluene under atmospheric pressure at from 25 to 30° C. for 20 hours. After the catalyst had been removed, the toluene solution was washed several times with water and dried with potassium carbonate, after which the toluene was distilled off. The residue was dissolved in isopropanol, and ethanolic hydrochloric acid was added. Crystallization from isopropanol gave 39.9 g (80%) of 5-[(3-trifluoromethylphenethyl)-methylamino]-2-(3,5-dimethoxyphenyl)-2-isopropylvaleronitrile of melting point 136°-138° C.

後処理

  1. customprepared
  2. customAfter the catalyst had been removed
  3. washthe toluene solution was washed several times with water
  4. dry with materialdried with potassium carbonate
  5. distillationafter which the toluene was distilled off
  6. dissolutionThe residue was dissolved in isopropanol
  7. additionethanolic hydrochloric acid was added
  8. customCrystallization from isopropanol

出典と根拠

ORDレコード
ord-1899f7c3a7d84a91ace19e0da60b5f40
出典データセット
uspto-grants-1990_11
特許番号
US04968717

反応ノート

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