Hydrochloric Acid → HCID 67226130, compound

HRID 629667Notes

Reaction equation

HRID 629667 reaction equation
[H-].[Na+].[Br-].[Br:4][C:5]1[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=1[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:32]1[CH2:37][CH2:36][N:35]([C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[C:40]([O:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:39]=2)[CH2:34][CH2:33]1.Cl>CS(C)=O>[Br:4][C:5]1[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=1[CH:7]=[C:32]1[CH2:33][CH2:34][N:35]([C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[C:40]([O:48][C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH:39]=2)[CH2:36][CH2:37]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 11733967Phosphonium, [(2-bromophenyl)methyl]triphenyl-, bromideHCID 67226770HCID 67226770, compound

Product 1

HCID 67226130HCID 67226130, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Dimethylsulfoxide (22.88 mL) with sodium hydride (0.332 g) was heated to 70 OC for 1 hour, then cooled to room temperature and (2-bromobenzyl)triphenylphosphonium bromide (3.40 g) was added in several portions, and then stirred at room temperature for 1 hour. A solution of methyl 4-(4-oxopiperidin-1-yl)-2-phenoxybenzoate (1.8 g) in dimethylsulfoxide (5.20 mL) was then added and the reaction was heated to 70° C. over the weekend. The reaction was acidified with 1M aqueous HCl solution and extracted with ether. The combined extracts were washed thoroughly with water and brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by flash chromatography eluting with 0-20% ethyl acetate in hexanes.

Workup

  1. temperaturethe reaction was heated to 70° C. over the weekend
  2. extractionextracted with ether
  3. washThe combined extracts were washed thoroughly with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography
  8. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7967f07b1d504aa295dc960041bff6b8
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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