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

HRID 1606781Notes

Reaction equation

HRID 1606781 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
180 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d58de6d27fe040538899deb8fcb4ce27
Source dataset
uspto-grants-1976_04
Patent number
US03953596

Reaction notes

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