Dimethylformamide → HCID 131715264, compound

HRID 2309640Notes

Reaction equation

HRID 2309640 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[N:9]([CH3:10])N=NN=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:35]CN)[CH2:31][CH2:30]2)=[CH:14][CH:13]=1.[C:38](=[O:41])([O-:40])[O-:39].[Na+].[Na+].CN(C)C=[O:47]>O>[C:5]([OH:4])(=[O:47])[C:38]([OH:40])=[O:41].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:10][N:9]3[CH2:2][CH2:3][O:4][C:5]3=[O:39])[CH2:31][CH2:30]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 14518041HCID 14518041, compoundHCID 14518104HCID 14518104, compound

Product 1

HCID 131715264HCID 131715264, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4 parts of 5-(2-bromoethoxy)-1-methyl-1H-tetrazole, 5.5 parts of 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimdazol-2-yl]methyl]-1-piperidineethanamine, 2.3. parts of sodium carbonate and 45 parts of N,N-dimethylformamide was stirred overnight at 70° C. The reaction mixture was poured into water. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in ethanol. The salt was filtered off and dried, yielding 1.3 parts (13%) of 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]2-oxazolidinone ethanedioate(2:5); mp. 147.9° C. (385).

Workup

  1. extractionThe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customdried

Sources & evidence

ORD record
ord-ac0cfbb685bc4e5183eb8ae6b0368042
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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