Ethanol → HCID 12891722, compound

HRID 1856570Notes

Reaction equation

HRID 1856570 reaction equation
S1C=CC=C1.C(O)C.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:18]2[NH:26][CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-])=O)=[CH:37][CH:36]=3)[CH2:29][CH2:28]2)=[CH:12][CH:11]=1.[H][H]>[Pt].CO>[NH2:41][C:38]1[CH:39]=[CH:40][C:35]([CH2:34][CH2:33][N:30]2[CH2:29][CH2:28][CH:27]([NH:26][C:18]3[N:17]([CH2:16][C:13]4[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]=3)[CH2:32][CH2:31]2)=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8030ThiopheneHCID 12891532HCID 12891532, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12891722HCID 12891722, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol are added 3.3 parts of 1-(4-fluorophenylmethyl)-N-{1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl}-1H-benzimidazol-2-amine and 120 parts of methanol. The whole is hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of methylbenzene and methanol (95:5 by volume) saturated with ammonia, as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2-propanol, yielding 1.3 parts (42%) of N-{1-[2-(4-aminophenyl)ethyl]-4-piperidinyl}-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine; mp. 195.4° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of methylbenzene and methanol (95:5 by volume) saturated with ammonia
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-0434d351c44543548595f1b305260dff
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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