Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 20298797, compound

HRID 1389308Notes

Reaction equation

HRID 1389308 reaction equation
[C:1]1([CH:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([NH2:24])[C:18]([NH:21][CH2:22][CH3:23])=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:32](=N)(OCC)[CH3:33]>C(O)(=O)C>[C:25]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]4[N:21]([CH2:32][CH3:33])[C:22]([CH3:23])=[N:24][C:17]=4[CH:16]=3)[CH2:12][CH2:13]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 30178804-{[4-(Diphenylmethyl)piperazin-1-yl]methyl}-N~1~-ethylbenzene-1,2-diamine

Product 1

HCID 20298797HCID 20298797, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.8 parts of 4-[4-(diphenylmethyl)-1-piperazinylmethyl]-N1 -ethyl-1,2-benzenediamine and 25 parts of acetic acid is stirred at room temperature till all solid enters solution. Then there are added 1.73 parts of ethyl ethanimidate hydrochloride and stirring is continued first for one hour at room temperature and further for one hour at reflux. The reaction mixture is evaporated and the residue is stirred in water. The whole is alkalized with a sodium hydroxide solution and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 2.7 parts of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-ethyl-2-methyl-1H-benzimidazole; mp. 152.9° C.

Workup

  1. stirringstirring
  2. temperatureat reflux
  3. customThe reaction mixture is evaporated
  4. stirringthe residue is stirred in water
  5. extractionthe product is extracted with dichloromethane
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customThe residue is crystallized from 4-methyl-2-pentanone
  14. filtrationThe product is filtered off
  15. customdried

Sources & evidence

ORD record
ord-180c5734806d4b8f9001cc409cba913e
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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