Hydrochloric Acid → (s)-n,n-Dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine-hydrochloride

HRID 2234234

反応式

HRID 2234234 の反応式
C(N(C(C)C)CC)(C)C.[CH3:10][N:11]([CH3:31])[CH2:12][CH2:13][C@H:14]([O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1.C1(OC([Cl:41])=O)C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[ClH:41].[CH3:10][N:11]([CH2:12][CH2:13][C@H:14]([O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH3:31]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9818212(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

生成物 1

HCID 44137750(s)-n,n-Dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine-hydrochloride

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

Diisopropylethylamine (210 ml) is added to a solution of (S)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)-propanamine (311 g; 99.6% ee) in toluene (1200 ml) and then phenylchloroformate (150 ml) is added at 60° C. After stirring at 80° C. for two hours, the mixture is cooled down, shaken with a diluted solution of hydrochloric acid, water and a 2% solution of sodium hydrogencarbonate. The organic phase is dried with sodium sulfate and evaporated. The evaporation residue is dissolved in ethanol (300 ml) and a 5M solution of potassium hydroxide (400 ml) is added drop by drop under reflux. After refluxing for two hours, the mixture is evaporated to half the volume, diluted with water (1,000 ml) and extracted with toluene (300 ml). The organic phase is dried with sodium sulfate and evaporated. The evaporation residue is dissolved in ethanol (300 ml), ammonium chloride is added (80 g) and the mixture is refluxed for two hours. The mixture is then evaporated to dryness, toluene (1,000 ml) is added, and the mixture is filtered while hot. After cooling to lab temperature, the precipitated light-brownish crystals are sucked off. The yield is 183 g (55%), b.p. 167-169° C.

後処理

  1. temperaturethe mixture is cooled down
  2. dry with materialThe organic phase is dried with sodium sulfate
  3. customevaporated
  4. dissolutionThe evaporation residue is dissolved in ethanol (300 ml)
  5. additiona 5M solution of potassium hydroxide (400 ml) is added drop by drop
  6. temperatureunder reflux
  7. temperatureAfter refluxing for two hours
  8. customthe mixture is evaporated to half the volume
  9. additiondiluted with water (1,000 ml)
  10. extractionextracted with toluene (300 ml)
  11. dry with materialThe organic phase is dried with sodium sulfate
  12. customevaporated
  13. dissolutionThe evaporation residue is dissolved in ethanol (300 ml)
  14. additionammonium chloride is added (80 g)
  15. temperaturethe mixture is refluxed for two hours
  16. customThe mixture is then evaporated to dryness, toluene (1,000 ml)
  17. additionis added
  18. filtrationthe mixture is filtered while hot
  19. temperatureAfter cooling to lab temperature

出典と根拠

ORDレコード
ord-8e5e9657ad494c829b2d6f56094a30c8
出典データセット
uspto-grants-2010_05
特許番号
US07709662B2

関連ノート

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