Ethanol → HCID 70575295, compound

HRID 1389322Notes

Reaction equation

HRID 1389322 reaction equation
S1C=CC=C1.C([OH:8])C.Cl.Cl.Cl.Cl[CH:13]([C:34]1[CH:45]=[CH:44][C:37]2[N:38]([CH2:42][CH3:43])[C:39]([CH3:41])=[N:40][C:36]=2[CH:35]=1)[CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.[H][H]>[Pd].CO>[OH2:8].[C:28]1([CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][C:34]3[CH:45]=[CH:44][C:37]4[N:38]([CH2:42][CH3:43])[C:39]([CH3:41])=[N:40][C:36]=4[CH:35]=3)[CH2:16][CH2:17]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8030ThiopheneHCID 20298704HCID 20298704, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70575295HCID 70575295, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2 parts of a solution of 2 parts of thiophene in 40 parts of ethanol, are added 9 parts of 5-{1-chloro-2-[4-(diphenylmethyl)-1-piperazinyl]ethyl}-1-ethyl-2-methyl-1H-benzimidazole trihydrochloride and 240 parts of methanol. The whole is hydrogenated at normal pressure and at room temperature with 4 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is taken up in 100 parts of water and the whole is alkalized with ammonium hydroxide. The product is extracted twice with dichloromethane. The combined extracts are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2-propanol. The product is filtered off and dried, yielding 2.4 parts (35.5%) of 5-{2-[4 -(diphenylmethyl)-1-piperazinyl]ethyl}-1-ethyl-2-methyl-1H-benzimidazole monohydrate; mp. 95°-105° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. extractionThe product is extracted twice with dichloromethane
  4. customThe combined extracts are dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from 2-propanol
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-6a40ef2237e9480bb73903cfce934283
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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