Saccharin → HCID 67809422, compound

HRID 2211141Notes

Reaction equation

HRID 2211141 reaction equation
[H-].[Na+].[S:3]1([C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7](=[O:8])[NH:6]1)(=[O:5])=[O:4].[Cl:15][C:16]1[CH:17]=[C:18]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33]Cl)[CH2:28][CH2:27]2)[C:19]2[O:24][CH2:23][CH2:22][O:21][C:20]=2[CH:25]=1>CN(C=O)C>[ClH:15].[Cl:15][C:16]1[CH:17]=[C:18]([N:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][N:6]3[C:7](=[O:8])[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[S:3]3(=[O:4])=[O:5])[CH2:30][CH2:31]2)[C:19]2[O:24][CH2:23][CH2:22][O:21][C:20]=2[CH:25]=1

Participants

5

Reactant 3

HCID 5143SaccharinHCID 24758Sodium hydrideHCID 19375627HCID 19375627, compound

Product 1

HCID 67809422HCID 67809422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of sodium hydride (0.31 g, 13 mmol) in 12 ml of dry DMF was added saccharin (2.29 g, 13 mmol) in 12 ml of dry DMF. Stirring was continued for 10 minutes before 1-(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)-4-(2-chloroethyl)piperazine (4.12 g, 13 mmol) (which can be obtained as described in EP-A-0190472) in 20 ml of dry DMF was added. The reaction mixture was heated under a nitrogen atmosphere for 7 hours, cooled down and extracted with ethylacetate (3×100 ml). The combined organic layers were washed with 5% NaHCO3, brine, dried and the solvent was removed in vacuo. The crude product was purified by flash column chromatography (silicagel/acetone:hexane=1:3) and the so-obtained free base was converted to its hydrochloride salt. Yield 3.13 g, (50%), m.p. 267°-70° C.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated under a nitrogen atmosphere for 7 hours
  3. temperaturecooled down
  4. extractionextracted with ethylacetate (3×100 ml)
  5. washThe combined organic layers were washed with 5% NaHCO3, brine
  6. customdried
  7. customthe solvent was removed in vacuo
  8. customThe crude product was purified by flash column chromatography (silicagel/acetone:hexane=1:3)

Sources & evidence

ORD record
ord-f8692c2f88744d3ea5aabccc5233b68c
Source dataset
uspto-grants-1995_10
Patent number
US05462942

Reaction notes

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