Hydrochloric Acid → HCID 20288026, compound

HRID 126874Notes

Reaction equation

HRID 126874 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:32])[CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21](C(C)=C)[C:20]3=[O:31])[CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.Cl.C(O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:32])[CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[O:31])[CH2:14][CH2:15]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 20288041HCID 20288041, compound

Product 1

HCID 20288026HCID 20288026, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9 parts of 1-[3-[4-[2-(3-chlorophenyl)-2-oxoethyl]-1-piperidinyl]propyl]-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 18 parts of a concentrated hydrochloric acid, 80 parts of ethanol and 50 parts of water is stirred for 30 minutes at room temperature. The reaction mixture is evaporated and water is added to the residue. The free base is liberated in the conventional manner with ammonium hydroxide and extracted with trichloromethane. The extract is dried, filtered and evaporated. The oily 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. The product is filtered off and dried, yielding 6.4 parts (78%) of 1 -[3-[4-[2-(3-chlorophenyl)-2-oxoethyl]-1-piperidinyl]propyl]-1,3-dihydro-2H-benzimidazol-2-one; mp. 160.3° C.

Workup

  1. customThe reaction mixture is evaporated
  2. additionwater is added to the residue
  3. extractionextracted with trichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from 4-methyl-2-pentanone
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-5e0430b2d75842dcbdcf4fd06c5c697e
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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