Methanol → HCID 44301216, compound

HRID 1856563Notes

Reaction equation

HRID 1856563 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][CH:9]2[CH2:11][O:10]2)=[CH:5][CH:4]=1.Br.Br.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[C:25]2[NH:33][CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].CO>C1C=CC=CC=1>[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[C:25]2[NH:33][CH:34]2[CH2:35][CH2:36][N:37]([CH2:11][CH:9]([CH2:8][O:7][C:6]3[CH:12]=[CH:13][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[OH:10])[CH2:38][CH2:39]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 166462,3-Epoxypropyl 4'-methoxyphenyl etherHCID 3018631Norastemizole hydrobromide

Product 1

HCID 44301216HCID 44301216, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3.6 parts of [(4-methoxyphenoxy)methyl]oxirane, 4.9 parts of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide, 2.1 parts of sodium carbonate, 40 parts of methanol and 90 parts of benzene is stirred and refluxed overnight. The reaction mixture is filtered and the filtrate is evaporated. The residue is crystallized from a mixture of 2-propanone and 2,2'-oxybispropane. The product is filtered off and dried, yielding 2.6 parts (51%) of 4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-α-(4-methoxyphenoxymethyl)-1-piperidineethanol; mp. 174.5° C.

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. customThe residue is crystallized from a mixture of 2-propanone and 2,2'-oxybispropane
  5. filtrationThe product is filtered off
  6. customdried

Sources & evidence

ORD record
ord-fe2d666d1f484a2bb69fe7a7951526a7
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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