Isopropanol → 2-(4-piperidinylmethyl)-1-(2-thienylmethyl)-1H-benzimidazole

HRID 2309626Notes

Reaction equation

HRID 2309626 reaction equation
ClC1N=CN=C2C=1N=C(C)N2C.Cl.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][N:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][CH:30]1[CH2:35][CH2:34][N:33](C(OCC)=O)[CH2:32][CH2:31]1.[OH-].[K+].CC(O)C>O>[NH:33]1[CH2:34][CH2:35][CH:30]([CH2:29][C:21]2[N:20]([CH2:19][C:15]3[S:14][CH:18]=[CH:17][CH:16]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:22]=2)[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 10845171HCID 10845171, compoundHCID 14012872HCID 14012872, compound

Product 1

HCID 140128742-(4-piperidinylmethyl)-1-(2-thienylmethyl)-1H-benzimidazoleYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 68 parts of ethyl 4-[[1-(2-thienylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidinecarboxylate monohydrochloride, 95 parts of potassium hydroxide, 800 parts of 2-propanol and 10 parts of water was stirred and refluxed for 6 hours. The reaction mixture was evaporated and water was added to the residue. The product was extracted with methylbenzene. The extract was dried, filtered and evaporated. The residue was crystallized from 1,1'-oxybisethane. The product was filtered off and dried, yielding 27 parts (49%) of 2-(4-piperidinylmethyl)-1-(2-thienylmethyl)-1H-benzimidazole; mp. 117.4° C. (64).

Workup

  1. temperaturerefluxed for 6 hours
  2. customThe reaction mixture was evaporated
  3. additionwater was added to the residue
  4. extractionThe product was extracted with methylbenzene
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from 1,1'-oxybisethane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-c42cc502ad1a4def98db1b2cacc8aaad
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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