Ethylene Glycol → HCID 69843245, compound

HRID 1596465Notes

Reaction equation

HRID 1596465 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[C:16](=O)[CH:10]([CH2:11][N:12]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([OH:28])[CH2:26][OH:27].CC1C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:18]([N:12]1[CH2:13][CH:14]2[CH2:16][C:10]3([O:27][CH2:26][CH2:25][O:28][CH:11]13)[CH2:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:15]2)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 3671723,7-Dibenzyl-3,7-diazabicyclo[3.3.1]nonan-9-one

Product 1

HCID 69843245HCID 69843245, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3,7-dibenzyl-3,7-diazabicyclo[3.3.1]nonane-9-one (10.0 g; 29.8 mmol; Bionet), ethylene glycol (20 g) and p-TSA (12.5 g; 65.7 mmol) in toluene (200 mL) was refluxed in a Dean-Stark apparatus for 12 h. NaOH (200 mL, 2M) was added and the organic layer separated, dried and concentrated to give the sub-title compound in a quantitative yield.

Workup

  1. customthe organic layer separated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-882240df5fd64fa98cd1e5fe8b01fd92
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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