((o-Methoxyphenoxy)methyl)oxirane → HCID 53872367, compound

HRID 2051690Notes

Reaction equation

HRID 2051690 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]1[CH2:9][O:8]1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]2[NH:22][C:21](=[O:23])[N:20]([CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]3)[C:19]=2[CH:31]=1>CC(O)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]2[NH:22][C:21](=[O:23])[N:20]([CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][N:27]([CH2:9][CH:7]([OH:8])[CH2:6][O:5][C:4]4[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=4[O:2][CH3:1])[CH2:26]3)[C:19]=2[CH:31]=1

Participants

4

Reactant 2

HCID 98357((o-Methoxyphenoxy)methyl)oxiraneHCID 20379505HCID 20379505, compound

Product 1

HCID 53872367HCID 53872367, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4 parts of [(2-methoxyphenoxy)methyl]oxirane, 5.3 parts of 6-chloro-1,3-dihydro-1-(3-piperidinylmethyl)-2H-benzimidazol-2-one and 120 parts of 2-propanol is stirred and refluxed for 5 hours. The reaction mixture is cooled and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and crystallized from 4-methyl-2-pentanone, yielding 2.5 parts (28%) of 6-chloro-1,3-dihydro-1-{1-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-3-piperidinylmethyl}-2H-benzimidazol-2-one; mp. 167° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture is cooled
  3. customevaporated
  4. customThe residue is purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. customThe residue is crystallized from 4-methyl-2-pentanone and 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-e75dca52ae4d4d3f959219322a00f5dc
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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