Dimethylformamide → HCID 21473726, compound

HRID 2293999Notes

Reaction equation

HRID 2293999 reaction equation
Cl.[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.[C:18](=[O:21])([O-])[O-].[Na+].[Na+].[CH3:24][N:25]([CH3:28])[CH:26]=[O:27]>>[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:4][CH2:5][C:6]4[C:26](=[O:27])[N:25]5[CH2:28][CH2:16][CH2:17][CH:3]([O:21][CH3:18])[C:24]5=[N:8][C:7]=4[CH3:10])[CH2:14][CH2:15]3)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 11334359R-56109 hydrochloride

Product 1

HCID 21473726HCID 21473726, compoundYield 36%

Procedure

A mixture of intermediate (13) (0.012 mol), 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole monohydrochloride (0.010 mol) and sodium carbonate (0.025 mol) in N,N-dimethylformamide (50 ml) was stirred for 6 hours at 80°-90° C. The reaction mixture was filtered and the filtrate was evaporated. Water was added to the residue and this mixture was extracted with dichloromethane. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from acetonitrile/2,2'-oxybispropane. The crystals were filtered off and dried, yielding 1.6 g (36%) of (±)-3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-methoxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 130.8° C. (comp. 7).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. additionWater was added to the residue
  4. extractionthis mixture was extracted with dichloromethane
  5. dry with materialThe separated organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from acetonitrile/2,2'-oxybispropane
  12. filtrationThe crystals were filtered off
  13. customdried

Sources & evidence

ORD record
ord-b60085862faa4406bf7ac8680a65e7f8
Source dataset
uspto-grants-1997_11
Patent number
US05688799

Reaction notes

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