Hydrochloric Acid → HCID 69411401, compound

HRID 1272346Notes

Reaction equation

HRID 1272346 reaction equation
CS([Cl:5])(=O)=O.[CH2:6](O)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH3:22][C:23]1([CH3:46])[CH:27]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:26]2[C:33]([CH3:45])=[C:34]([N:39]3[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)[C:35]([CH3:38])=[C:36]([CH3:37])[C:25]=2[O:24]1.[ClH:47]>C(#N)C.C(OCC)(=O)C>[ClH:5].[ClH:47].[CH3:22][C:23]1([CH3:46])[CH:27]([N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[C:26]2[C:33]([CH3:45])=[C:34]([N:39]3[CH2:40][CH2:41][N:42]([CH2:6][CH2:7][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:43][CH2:44]3)[C:35]([CH3:38])=[C:36]([CH3:37])[C:25]=2[O:24]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 60542-PhenylethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 9902690HCID 9902690, compound

Product 1

HCID 69411401HCID 69411401, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.09 mL, 1.2 mmol) was added to a solution of phenethyl alcohol (0.14 mL, 1.2 mmol) and triethylamine (0.21 mL, 1.5 mmol) in acetonitrile (5 ml) at room temperature. The mixture was stirred for 1 hour, and then (2,2,4,6,7-pentamethyl-3-pyrrolidinyl-2,3-dihydro-1-benzofuran-5-yl)piperazine obtained in Example 134 (343 mg, 1 mmol) was added. After stirring for 16 hours at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified with basic silica gel column chromatography (ethyl acetate/hexan=4/1) to obtain 166 mg as a free base. The free base was treated with 4N hydrogenchloride in ethyl acetate to obtain 96 mg (yield 18%) of the title compound. mp. 176–180° C. (decomposition) (ethanol-ethyl acetate).

Workup

  1. stirringAfter stirring for 16 hours at room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified with basic silica gel column chromatography (ethyl acetate/hexan=4/1)
  10. customto obtain 166 mg as a free base

Sources & evidence

ORD record
ord-e434735fe5c04e64bb0184ad14b3d434
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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