Dimethylformamide → HCID 86743334, compound

HRID 1085694Notes

Reaction equation

HRID 1085694 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][NH:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[OH:20])[CH2:14][CH2:13]1.[C:30](Cl)(=[O:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[OH-:42].[Na+].CN(C)[CH:46]=[O:47]>>[C:46]([OH:47])(=[O:40])/[CH:18]=[CH:19]\[C:21]([OH:22])=[O:42].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([O:20][C:30](=[O:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 66982Decanoyl chlorideHCID 20060592HCID 20060592, compound

Product 1

HCID 86743334HCID 86743334, compoundYield 16%

Procedure

To a stirred and hot (60° C.) solution of 4.2 parts of 4-[(2-benzothiazolyl)methylamino]-α-[(4-fluorophenoxy)methyl]-1-piperidineethanol in 90 parts of N,N-dimethylformamide were added dropwise 2.3 parts of decanoyl chloride. Upon completion, stirring was continued for 24 hours at 60° C. After cooling to room temperature, the reaction mixture was poured onto water and the whole was treated with sodium hydroxide. The aqueous phase was decanted and the residual product was washed three times with water and dissolved in trichloromethane. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (Z)-2-butenedioate salt in a mixture of 2-propanone and 2,2'-oxybispropane. The salt was filtered off and dried, yielding 1.1 parts (16%) of [2-[4-[(2-benzothiazolyl)methylamino]-1-piperidinyl]-1-[(4-fluorophenoxy)-methyl]ethyl]decanoate (Z)-2-butenedioate(1:1); mp. 134.2° C. (454).

Workup

  1. stirringUpon completion, stirring
  2. additionthe reaction mixture was poured onto water
  3. customThe aqueous phase was decanted
  4. washthe residual product was washed three times with water
  5. dissolutiondissolved in trichloromethane
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. additionThe residue was converted into the (Z)-2-butenedioate salt in a mixture of 2-propanone and 2,2'-oxybispropane
  14. filtrationThe salt was filtered off
  15. customdried

Sources & evidence

ORD record
ord-0a578bcd902a4b1cbdb204be382ff909
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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