O-methyl 1-(phenylmethyl)-4-piperidineethanimidate dihydrochloride → HCID 14012846, compound

HRID 2309617Notes

Reaction equation

HRID 2309617 reaction equation
Cl.Cl.[C:3]1([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17](=[NH:20])OC)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][NH:27][C:28]1[C:29](N)=[CH:30][CH:31]=[CH:32][CH:33]=1>C(O)(=O)C>[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][N:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:20]=[C:17]1[CH2:16][CH:13]1[CH2:12][CH2:11][N:10]([CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 14518101O-methyl 1-(phenylmethyl)-4-piperidineethanimidate dihydrochlorideHCID 14518102HCID 14518102, compound

Product 1

HCID 14012846HCID 14012846, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 27.3 parts of O-methyl 1-(phenylmethyl)-4-piperidineethanimidate dihydrochloride, 14 parts of N-(2-furanylmethyl)-1,2-benzenediamine and 250 parts of acetic acid was stirred overnight at room temperature. The reaction mixture was evaporated and water was added to the residue. The whole was alkalized with sodium carbonate and extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from 1,1'-oxybisethane. The product was filtered off and dried, yielding 15.5 parts (57%) of 1-(2-furanylmethyl)-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole; mp. 124.8° C. (3).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater was added to the residue
  3. extractionextracted with 4-methyl-2-pentanone
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 1,1'-oxybisethane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-a0c6451e15034311a4eeb0a10f29fc11
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

Loading…