Acetic Acid → HCID 131711666, compound

HRID 1448104Notes

Reaction equation

HRID 1448104 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][C:3]=1[NH:28][CH2:29][CH2:30][CH2:31][OH:32].Cl.[C:34]1([C:40](=N)OCC)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[C:45](O)(=[O:47])[CH3:46]>>[C:22]1([CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]2[CH2:11][CH2:10][N:9]([CH2:8][C:6]3[CH:5]=[CH:4][C:3]4[N:28]([CH2:29][CH2:30][CH2:31][O:32][C:45](=[O:47])[CH3:46])[C:40]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[N:1][C:2]=4[CH:7]=3)[CH2:14][CH2:13]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)HCID 20298713HCID 20298713, compound

Product 1

HCID 131711666HCID 131711666, compoundYield 24.8%

Procedure

A mixture of 5.6 parts of 3-[{2-amino-4-[4-(diphenylmethyl)-1-piperazinylmethyl]phenyl}amino]-1-propanol, 2.8 parts of ethyl benzenecarboximidate hydrochloride and 50 parts of acetic acid is stirred first overnight at room temperature and further for 1 hour at reflux. The solvent is evaporated in vacuo and the residue is stirred in water. The whole is alkalized with ammonium hydroxide and the product is extracted with trichloromethane. 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 fractions with the highest Rf-value are collected and the eluent is evaporated. The residue is crystallized from 35 parts of 2,2'-oxybispropane. The product is filtered off and dried, yielding 1.8 parts (24.8%) of [3-{5-[4-(diphenylmethyl)-1-piperazinylmethyl]-2-phenyl-1H-benzimidazol-1-yl}propyl]acetate; mp. 111.5° C.

Workup

  1. temperatureat reflux
  2. customThe solvent is evaporated in vacuo
  3. stirringthe residue is stirred in water
  4. extractionthe product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (98.2 by volume) as eluent
  10. customThe fractions with the highest Rf-value are collected
  11. customthe eluent is evaporated
  12. customThe residue is crystallized from 35 parts of 2,2'-oxybispropane
  13. filtrationThe product is filtered off
  14. customdried

Sources & evidence

ORD record
ord-35bd816641c8498e98b9ee63b3a6c1bf
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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