Phenyl glycidyl ether → HCID 19911532, compound

HRID 1085869Notes

Reaction equation

HRID 1085869 reaction equation
[O:1]([CH2:8][CH:9]1[CH2:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:14][CH2:15][CH2:16][N:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[N:19]=[C:18]1[CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH3:13]>CC(O)C>[CH2:12]([O:14][CH2:15][CH2:16][N:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[N:19]=[C:18]1[CH2:26][N:27]1[CH2:28][CH2:29][N:30]([CH2:11][CH:9]([CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:10])[CH2:31][CH2:32]1)[CH3:13]

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 19911564HCID 19911564, compound

Product 1

HCID 19911532HCID 19911532, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1.65 parts of 2-(phenoxymethyl)oxirane, 8.9 parts of 3-(2-ethoxyethyl) -2-(1-piperazinylmethyl)-3H-imidazo[4,5-b]pyridine and 40 parts of 2-propanol was stirred for 20 hours at reflux temperature. The reaction mixture was evaporated and the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.36 parts (31.0%) of 4-[[3-(2-ethoxyethyl)-3Himidazo[4,5-b]pyridin-2-yl]methyl]-α-(phenoxymethyl)-1-piperazineethanol; mp. 102.5° C. (compound 118).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from 2,2'-oxybispropane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-c3baf3bffada4d52812708773c2e3205
Source dataset
uspto-grants-1991_04
Patent number
US05011842

Reaction notes

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