Dimethyl Sulfoxide → HCID 9933466, compound

HRID 635221Notes

Reaction equation

HRID 635221 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:43]=[CH:42][C:15]2[C:16]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][O:28][C:29]4[CH:38]=[C:37]5[C:32]([C:33](=[O:41])[C:34]([CH2:39][OH:40])=[CH:35][O:36]5)=[CH:31][CH:30]=4)[CH2:21][CH2:20]3)=[N:17][O:18][C:14]=2[CH:13]=1.C(N(CC)CC)C>ClCCl.O>[F:11][C:12]1[CH:43]=[CH:42][C:15]2[C:16]([CH:19]3[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][CH2:27][O:28][C:29]4[CH:38]=[C:37]5[C:32]([C:33](=[O:41])[C:34]([CH:39]=[O:40])=[CH:35][O:36]5)=[CH:31][CH:30]=4)[CH2:23][CH2:24]3)=[N:17][O:18][C:14]=2[CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3037308Abaperidone

Product 1

HCID 9933466HCID 9933466, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2 mL (23 mmoles) of oxalyl chloride in 35 mL of dry dichloromethane, cooled at −70°C., was added drop by drop a solution of 3 mL (42 mmoles) of dimethyl sulfoxide dissolved in 10 mL of dichloromethane and the mixture was stirred for 5 minutes. Then 5 g (11 mmoles) of 7-[3-[4-(6-fluorobenzo[d]isoxazole-3-yl)piperidin-1-yl]propoxy]-3-(hydroxymethyl)-chromen-4-one (Patent ES 9600323) were added in several portions for 15 minutes and stirred for further 30 minutes at −70° C. 15 mL (107 moles) of triethylamine were added drop by drop and stirred overnight while allowed to warm to room temperature gradually. By cooling at −20° C., 50 mL of water were added, the mixture was allowed to warm to room temperature and the organic phase was decanted, dried over sodium sulphate and evaporated. The solid obtained was purified by chromatography on a silica gel column. Elution of the column with CHCl3:CH3OH (98:2, v/v) gave 2.12 g of 7-[3-[4-(6-fluorobenzo[d]isoxazole-3-yl)piperidin-1-yl]propoxy]-3-formyl-chromen-4-one in 43% yield, mp 163-5° C.

Workup

  1. stirringstirred for further 30 minutes at −70° C
  2. stirringstirred overnight
  3. temperatureBy cooling at −20° C.
  4. temperatureto warm to room temperature
  5. customthe organic phase was decanted
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe solid obtained
  9. customwas purified by chromatography on a silica gel column
  10. washElution of the column with CHCl3:CH3OH (98:2

Sources & evidence

ORD record
ord-25dfd4b4c48c46f3a03c82152a8633e9
Source dataset
uspto-grants-2001_02
Patent number
US06187793B1

Reaction notes

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