Triglyme → 3-(p-Chlorophenethyl)-8-oxa-3-azabicyclo(3.2.1)octane

HRID 1606781

反応式

HRID 1606781 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.S(O[CH2:22][CH:23]1[CH2:27][CH2:26][CH:25]([CH2:28]OS(C2C=CC(C)=CC=2)(=O)=O)[O:24]1)(C1C=CC(C)=CC=1)(=O)=O.COCCOCCOCCOC.[OH-].[Na+]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][N:8]2[CH2:28][CH:25]3[O:24][CH:23]([CH2:27][CH2:26]3)[CH2:22]2)=[CH:4][CH:3]=1

参加物

5

反応物 4

HCID 8189TriglymeHCID 14798Sodium HydroxideHCID 674302-(4-Chlorophenyl)ethylamineHCID 259634(Tetrahydrofuran-2,5-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

生成物 1

HCID 215445553-(p-Chlorophenethyl)-8-oxa-3-azabicyclo(3.2.1)octane

反応条件

温度
180 °C

実験手順

p-Chlorophenethylamine (0.643 mole, 100 grams) was added to a mixture of 2,5-bis(tosyloxymethyl)tetrahydrofuran (0.214 mole, 99.6 grams) and 200 ml of Ansul 161 (triethylene glycol dimethyl ether) and stirred the reaction mixture for 3 hours at 180° C. The reaction mixture was cooled to room temperature and neutralized with a methanolic sodium hydroxide solution (0.429 mole, 17.14 grams NaOH in 200 ml CH3OH) while stirring for 15 minutes. The solvents and excess starting amine were distilled from the reaction mixture under aspirator pressure. The residue was filtered collecting the sodium p-toluenesulfonate. The filtrate was distilled collecting one fraction (terminal pot temperature 280° C./0.1 mm Hg). The distillate which solidified was recrystallized from methanol obtaining 3-(p-chlorophenethyl)-8-oxa-3-azabicyclo(3.2.1)octane.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringwhile stirring for 15 minutes
  3. distillationThe solvents and excess starting amine were distilled from the reaction mixture under aspirator pressure
  4. filtrationThe residue was filtered
  5. customcollecting the sodium p-toluenesulfonate
  6. distillationThe filtrate was distilled
  7. customcollecting one fraction (terminal pot temperature 280° C./0.1 mm Hg)
  8. customThe distillate which solidified was recrystallized from methanol

出典と根拠

ORDレコード
ord-d58de6d27fe040538899deb8fcb4ce27
出典データセット
uspto-grants-1976_04
特許番号
US03953596

関連ノート

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