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

HRID 1904829
Notes
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Reaction equation

HRID 1904829 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 108451716-chloro-8,9-dimethyl-9H-purineHCID 14012872HCID 14012872, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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-61aa3fec301d44b5b09ab7a3e4702d6e
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04839374

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes