Sodium Hydroxide → Tecastemizole

HRID 477655Notes

Reaction equation

HRID 477655 reaction equation
Br.Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[NH:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:6][CH:5]=1.[OH-].[Na+]>O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[NH:20][CH:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3018631Norastemizole hydrobromide

Product 1

HCID 123618TecastemizoleYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 Parts of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide were taken up in water. The free base was liberated with a sodium hydroxide solution 50% and extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was boiled in 2-propanone. The product was filtered off and dried, yielding 17 parts (87.5%) of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine; mp. 215.5° C. (intermediate 90).

Workup

  1. extractionextracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-b476c6b954114a22b19073ff71aa30ff
Source dataset
uspto-grants-1989_12
Patent number
US04888426

Reaction notes

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