Piperidine → HCID 10476162, compound

HRID 2103110Notes

Reaction equation

HRID 2103110 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[OH:16][C:17]1[C:22]2[O:23][C:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:25][C:21]=2[CH:20]=[C:19]([C:38](Cl)=[O:39])[CH:18]=1>C(Cl)Cl>[OH:16][C:17]1[C:22]2[O:23][C:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:25][C:21]=2[CH:20]=[C:19]([C:38]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:39])[CH:18]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 22475174HCID 22475174, compound

Product 1

HCID 10476162HCID 10476162, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Piperidine (0.3 ml, 2 mmol) and ethyl diisopropylamine (0.5 ml, 3 mmol) were dissolved in methylene chloride (10 ml). 7-Hydroxy-2,2-diphenyl-benzo[1,3]dioxole-5-carbonyl chloride (353 mg, 1 mmol) dissolved in methylene chloride (3 ml) was added dropwise at room temperature. The reaction was stirred at room temperature for 24 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was extracted with IN aqueous HCl solution, brine, dried over sodium sulfate and filtered. The solvent was evaporated and the residue purified by column chromatography on silica gel (20 g, 5% methanol in dichloromethane eluant) to yield the phenol as a white solid (180 mg, 45%).

Workup

  1. additionwas added dropwise at room temperature
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe organic layer was extracted with IN aqueous HCl solution, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customthe residue purified by column chromatography on silica gel (20 g, 5% methanol in dichloromethane eluant)

Sources & evidence

ORD record
ord-60c2d96fbf634e079ac612a2e9d0dc8a
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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