Dimethylformamide → HCID 131715264, compound

HRID 1904844Notes

Reaction equation

HRID 1904844 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

Conditions

Temperature
70 °C

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-piperdineethanamine, 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-ad7e28d4606946e0bc9353ce7e133d66
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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