O-ethyl 1-(phenylmethyl)-4-piperidineethanimidate hydrochloride → HCID 14012850, compound

HRID 2309618Notes

Reaction equation

HRID 2309618 reaction equation
Cl.[C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16](=[NH:20])OCC)[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][NH:29][C:30]2[C:31](N)=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:24][CH:23]=1>CO>[CH3:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][N:29]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=3[N:20]=[C:16]2[CH2:15][CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:14][CH2:13]2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14518093O-ethyl 1-(phenylmethyl)-4-piperidineethanimidate hydrochloride2×HCID 14518103HCID 14518103, compound

Product 1

HCID 14012850HCID 14012850, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 116.5 parts of O-ethyl 1-(phenylmethyl)-4-piperidineethanimidate hydrochloride, 61.5 parts of N1 -[(4-methylphenyl)methyl]-1,2-benzenediamine and 400 parts of methanol was stirred and refluxed overnight. Another portion of 40 parts of O-ethyl 1-(phenylmethyl)-4-piperidineethanimidate hydrochloride was added and stirring was continued for 4 hours at reflux. The reaction mixture was evaporated. Water was added to the residue. The solution was treated with ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 74.5 parts (63%) of 1-[(4-methylphenyl)methyl]-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole; mp. 124.2° C. (6).

Workup

  1. temperaturerefluxed overnight
  2. stirringstirring
  3. temperatureat reflux
  4. customThe reaction mixture was evaporated
  5. additionWater was added to the residue
  6. additionThe solution was treated with ammonium hydroxide
  7. extractionThe product was extracted with trichloromethane
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was crystallized from acetonitrile
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-a8ba8855c88441898f26ca14a030173e
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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