Sodium Hydroxide → HCID 54488722, compound

HRID 1534598Notes

Reaction equation

HRID 1534598 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[C:10]2[C:16]3=[N:17][CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=[C:15]3[CH2:14][CH2:13][C:12]3[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:11]2=3)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:35].[OH-].[Na+]>C(Cl)Cl>[C:1]([N+:4]1([O-:35])[CH2:9][CH2:8][C:7](=[C:10]2[C:16]3=[N:17][CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=[C:15]3[CH2:14][CH2:13][C:12]3[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:11]2=3)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 54437955HCID 54437955, compound

Product 1

HCID 54488722HCID 54488722, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 450 mg of 1-acetyl-4-(8-chloro-5,6-dihydro-3-(1,1-dimethylethyl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidine in 30 ml of dry methylene chloride at -10° C. and under a nitrogen atmosphere was added 260 mg of 3-chloroperoxybenzoic acid in four portions ten minutes apart (mCPBA). The reaction mixture was kept at -10° C. for 3 hours and then slowly warmed to room temperature. The next day the mixture was poured into 1.0 N aqueous sodium hydroxide and extracted 3 times with methylene chloride. The combined organic portions were dried over magnesium sulfate, filtered and concentrated in vacuo to give a product which was purified via flash chromatography and triturated with pentane to give 195 mg (42%) of the title compound as a glass.

Workup

  1. extractionextracted 3 times with methylene chloride
  2. dry with materialThe combined organic portions were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a product which
  6. customwas purified via flash chromatography
  7. customtriturated with pentane

Sources & evidence

ORD record
ord-57c184b8b8f3413098519c819c565854
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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