Hydrochloric Acid → HCID 13769726, compound

HRID 979940Notes

Reaction equation

I.CO[CH:4](OC)[CH2:5][NH:6][C:7]([NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:22]3[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=3[N:20]=2)[CH2:14][CH2:13]1)=[NH:8].Cl.[OH-].[Na+]>>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:23]2[C:22]3[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=3[N:20]=[C:19]2[NH:18][CH:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][NH:9][C:7]3[NH:6][CH:5]=[CH:4][N:8]=3)[CH2:13][CH2:14]2)=[CH:26][CH:27]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 178495983HCID 178495983, compound

Product 1

HCID 13769726HCID 13769726, compoundYield 26%

Procedure

A mixture of 12.5 parts of N-(2,2-dimethoxyethyl)-N'-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]guanidine monohydroiodide and 100 parts of a hydrochloric acid solution 10% was stirred and refluxed for 1 hour. The reaction mixture was poured onto crushed ice. The whole was treated with a sodium hydroxide solution. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The solid residue was crystallized from 4-methyl-2-pentanone. The product was filtered off and dried, yielding 2.3 parts (26%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-(1H-imidazol-2-ylamino)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 226.5° C. (compound 79).

Workup

temperaturerefluxed for 1 hour
additionThe reaction mixture was poured
customonto crushed ice
extractionThe product was extracted with dichloromethane
customThe extract was dried
filtrationfiltered
customevaporated
customThe solid residue was crystallized from 4-methyl-2-pentanone
filtrationThe product was filtered off
customdried

Sources & evidence

ORD record: ord-f70a945d2a154d8b8cc463db4b2706a0
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04634704

Reaction notes

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