Sodium Carbonate → HCID 54026505, compound

HRID 2051689Notes

Reaction equation

HRID 2051689 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.[NH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[NH:24][C:23]2=[O:31])[CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[OH:8][CH:7]([CH2:6][O:5][C:4]1[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=1[O:2][CH3:1])[CH2:9][N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[NH:24][C:23]2=[O:31])[CH2:16]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 98357((o-Methoxyphenoxy)methyl)oxiraneHCID 20379508HCID 20379508, compound

Product 1

HCID 54026505HCID 54026505, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.6 parts of 2-(2-methoxyphenoxymethyl)oxirane, 5.3 parts of 1,3-dihydro-1-(3-piperidinylmethyl)-2H-benzimidazol-2-one monohydrochloride, 6 parts of sodium carbonate and 80 parts of ethanol is stirred and refluxed for 6 hours. The reaction mixture is cooled, filtered 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 a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and recrystallized from 4-methyl-2-pentanone, yielding 1.8 parts (22%) of 1,3-dihydro-1-{1-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-3-piperidinylmethyl}-2H-benzimidazol-2-one; mp. 158.1° C.

Workup

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

Sources & evidence

ORD record
ord-29214a22aa1c46098c5c915e5e0f7dbd
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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