Sodium Carbonate → soluflazine

HRID 2185824Notes

Reaction equation

HRID 2185824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]2[C:18]([NH2:20])=[O:19])=[CH:4][CH:3]=1.[Cl:27][CH2:28][C:29]([NH:31][C:32]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:39])=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[ClH:27].[ClH:27].[NH2:20][C:18]([CH:13]1[N:12]([CH2:11][CH2:10][CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH2:17][CH2:16][N:15]([CH2:28][C:29]([NH:31][C:32]2[C:33]([Cl:39])=[CH:34][CH:35]=[CH:36][C:37]=2[Cl:38])=[O:30])[CH2:14]1)=[O:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 772062-Chloro-N-(2,6-dichlorophenyl)acetamideHCID 22452529HCID 22452529, compound

Product 1

HCID 163885soluflazineYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-[4-(4-fluorophenyl)-4-(3-pyridinyl)butyl]-2-piperazinecarboxamide (6.75 g), 2-chloro-N-(2,6-dichlorophenyl)acetamide (5.24 g), sodium carbonate (3.16 g) and DMF (143 ml) was stirred for 4 hours at 70° C. The reaction mixture was evaporated and water was added to the residue. After extraction with DCM, the combined organic layers were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel (eluent:CHCl3/CH3OH 95/5). The desired fractions were collected and the solvent was evaporated. The residue was dissolved in 2-propanol and DIPE and converted into the hydrochloride salt. The salt was filtered off and dried, yielding 2.23 g of 3-(amino-carbonyl)-N-(2,6-dichloro-phenyl)-4-[4-(4-fluorophenyl)-4-(3-pyridinyl)-butyl]-1-piperazineacetamide dihydrochloride.monohydrate (compound 14, mp. 226.3° C.).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater was added to the residue
  3. extractionAfter extraction with DCM
  4. washthe combined organic layers were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent:CHCl3/CH3OH 95/5)
  9. customThe desired fractions were collected
  10. customthe solvent was evaporated
  11. dissolutionThe residue was dissolved in 2-propanol
  12. filtrationThe salt was filtered off
  13. customdried

Sources & evidence

ORD record
ord-cd862f798dda42ba83114718b38633d4
Source dataset
uspto-grants-2002_06
Patent number
US06403589B1

Reaction notes

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