Ethylene Glycol → HCID 22506708, compound

HRID 25194Notes

Reaction equation

HRID 25194 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].Cl.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([NH2:22])[C:14]2[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([NH2:22])[C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[O:4][CH2:1][CH2:2][O:3]3)=[CH:16][CH:15]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 86584739(R*)-[(4-chlorophenyl)(4-formylphenyl)methyl]amine hydrochloride

Product 1

HCID 22506708HCID 22506708, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chiral (+)-{(4-chlorophenyl)[4-(1,3-dioxolan-2-yl)phenyl]methyl}amine may be obtained in the following manner: 3.95 cm3 of ethylene glycol are poured into a suspension of 18.16 g of chiral (R*)-[(4-chlorophenyl)(4-formylphenyl)methyl]amine hydrochloride, in 1000 cm3 of toluene, and 0.82 g of para-toluenesulfonic acid monohydrate is added. After stirring for 20 hours at the reflux temperature, the reaction medium is cooled, washed with a saturated aqueous sodium bicarbonate solution, with water and with a saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The residue obtained is purified on a silica gel column (particle size 0.04-0.06 mm, diameter 8.4 cm, height 21.5 cm) with, as eluent, a cyclohexane/ethyl acetate (30/70 by volume) mixture, collecting 250 cm3 fractions. Fractions 23 to 30 are concentrated to dryness under reduced pressure (2.7 kpa). 1.39 g of chiral (+)-{(4-chlorophenyl)-[4-(1,3-dioxolan-2-yl)phenyl]methyl}amine are obtained in the form of a yellow oil.

Workup

  1. temperaturethe reaction medium is cooled
  2. washwashed with a saturated aqueous sodium bicarbonate solution, with water and with a saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue obtained
  7. customis purified on a silica gel column (particle size 0.04-0.06 mm, diameter 8.4 cm, height 21.5 cm) with, as eluent
  8. customa cyclohexane/ethyl acetate (30/70 by volume) mixture, collecting 250 cm3 fractions
  9. concentrationFractions 23 to 30 are concentrated to dryness under reduced pressure (2.7 kpa)

Sources & evidence

ORD record
ord-e27e00e3912a4bd8b0dd36299e7678f0
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Reaction notes

Loading…