m-Chloroperbenzoic acid → HCID 131723691, compound

HRID 2298086Notes

Reaction equation

HRID 2298086 reaction equation
[Cl:1]C1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([S:33]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[O:34])=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2)=[O:16].[OH-].[Ca+2].[OH-]>ClCCl>[ClH:1].[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([S:33]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)(=[O:6])=[O:34])=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]12[CH2:20][CH:21]3[CH2:22][CH:23]([CH2:24][CH:25]([CH2:27]3)[CH2:26]1)[CH2:28]2)=[O:16]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 11502978HCID 11502978, compound

Product 1

HCID 131723691HCID 131723691, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (0.30 g) was added to a solution of 2-chloro-5-(piperidin-4-ylsulfinyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.30 g) in dichloromethane (10 ml). After 2 h calcium hydroxide (170 mg) was added and 30 min. later the salts removed by filtration. The filtrate was concentrated under reduced pressure to give a residue which was purified by silica gel chromatography (eluting with 0-2% ethanol in dichloromethane). The residue was dissolved in methanol (5 ml) and hydrochloric acid (0.25 ml of a 4N solution in dioxane) was added. After stirring at room temperature for 14 h, the solution was concentrated under reduced pressure and triturated with diethyl ether to yield the title compound (0.03 g).

Workup

  1. customremoved by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto give a residue which
  4. customwas purified by silica gel chromatography (eluting with 0-2% ethanol in dichloromethane)
  5. dissolutionThe residue was dissolved in methanol (5 ml)
  6. additionhydrochloric acid (0.25 ml of a 4N solution in dioxane) was added
  7. concentrationthe solution was concentrated under reduced pressure
  8. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-a2264b461b674d36ab204484d1058a20
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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