Dibenzylamine → HCID 11393011, compound

HRID 239722Notes

Reaction equation

HRID 239722 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]1[CH2:22][S:19](=[O:21])(=[O:20])[O:18][CH2:17]1>C1(C)C=CC=CC=1>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][CH2:16][CH2:22][S:19]([OH:21])(=[O:20])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 14264Propane sultone

Product 1

HCID 11393011HCID 11393011, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of dibenzylamine (9.8 mL, 50.8 mmol) in toluene (50 mL) was added 1,3-propane sultone (6.50 g, 53.3 mmol). The mixture was stirred at reflux for 3 h. A sticky paste was formed at the bottom of the flask. The reaction mixture was cooled to room temperature. The top layer was decanted; and the paste was partially dissolved in EtOAc with heating. The mixture was poured in a 10% EtOAc/Hexanes (200 mL). The mixture was heated and the paste was spread on the walls of the conical flask. The solvent was removed. This process was repeated twice. MeOH (75 mL) was added to the paste. The mixture was heated until a white solid appeared. The solid was collected by filtration, washed with cold MeOH, and dried in vacuo, affording compound AV, 7.03 g (43%).

Workup

  1. temperatureat reflux for 3 h
  2. customA sticky paste was formed at the bottom of the flask
  3. customThe top layer was decanted
  4. dissolutionand the paste was partially dissolved in EtOAc
  5. temperaturewith heating
  6. additionThe mixture was poured in a 10% EtOAc/Hexanes (200 mL)
  7. temperatureThe mixture was heated
  8. customThe solvent was removed
  9. additionMeOH (75 mL) was added to the paste
  10. temperatureThe mixture was heated until a white solid
  11. filtrationThe solid was collected by filtration
  12. washwashed with cold MeOH
  13. customdried in vacuo
  14. customaffording compound AV

Sources & evidence

ORD record
ord-239c989eadde42e9b8b6f7156a1d1795
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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