Phenethylamine → 5-phenethyl-hexahydro-1H-furo(3,4-c)pyrrole

HRID 1283611ノート

反応式

HRID 1283611 の反応式
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(O[CH2:21][CH:22]1[CH:26]([CH2:27]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][O:24][CH2:23]1)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>COCCOCCOCCOC>[CH2:1]([N:9]1[CH2:21][CH:22]2[CH2:23][O:24][CH2:25][CH:26]2[CH2:27]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 1001PhenethylamineHCID 14798Sodium HydroxideHCID 215185433,4-Bis(tosyloxymethyl)tetrahydrofuran

生成物 1

HCID 214211525-phenethyl-hexahydro-1H-furo(3,4-c)pyrrole

試薬・触媒・溶媒 1

HCID 8189Triglyme溶媒

実験手順

Phenethylamine (0.15 mole, 18.2 grams) was reacted with a mixture of the cis and trans isomers of 3,4-bis(tosyloxymethyl)tetrahydrofuran, represented by formulas (XIX), (0.05 mole, 22.0 grams) in 60 ml triethylene glycol dimethyl ether at 185°C. for 3 hours. The reaction mixture was cooled to room temperature and neutralized with 75 ml methanolic sodium hydroxide solution (0.10 mole, 4.0 grams). After the reaction mixture was concentrated under aspirator pressure, 150 ml diethyl ether was added and sodium tosylate (18.5 grams) was filtered. Vacuum distillation of the filtrate gave 5-phenethyl-hexahydro-1H-furo(3,4-c)pyrrole (6.9 grams, b.p. 111° to 112°C./0.12 mm Hg). 5-Phenethyl-hexahydro-1H-furo(3,4-c)pyrrole was dissolved in 700 ml anhydrous diethyl ether and anhydrous hydrogen chloride was bubbled through the solution. The resulting 5-phenethyl-hexahydro-1H-furo(3,4-c)pyrrole hydrochloride was filtered, washed with ether, and dried. The product obtained had a melting point of 176° to 177°C.

後処理

  1. concentrationAfter the reaction mixture was concentrated under aspirator pressure, 150 ml diethyl ether
  2. additionwas added
  3. filtrationsodium tosylate (18.5 grams) was filtered
  4. distillationVacuum distillation of the filtrate

出典と根拠

ORDレコード
ord-8640b69165ee4ca4a0950816b6e90e4a
出典データセット
uspto-grants-1976_08
特許番号
US03975532

反応ノート

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