m-Chloroperbenzoic acid → Ammonium Hydroxide

HRID 1591188Notes

Reaction equation

HRID 1591188 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:28][C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([Cl:27])=[N:25][CH:26]=4)[CH2:15][CH2:14]3)[CH2:12][C:11](=[O:29])[C:10]=2[CH:30]=1)(=[O:4])=[O:3].ClC1C=CC=C(C(OO)=[O:39])C=1.[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:28][C:13]3([CH2:14][CH2:15][N:16]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([Cl:27])=[N:25][CH:26]=4)[CH2:17][CH2:18]3)[CH2:12][C:11](=[O:29])[C:10]=2[CH:30]=1)(=[O:4])=[O:3].[NH4+:5].[OH-:39]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 190453726-Methanesulfonamido-3,4-dihydro-1'-[2-(2-chloro-pyrid-5-yl)ethyl]-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one

Product 2

HCID 14923Ammonium HydroxideHCID 190453726-Methanesulfonamido-3,4-dihydro-1'-[2-(2-chloro-pyrid-5-yl)ethyl]-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The N-oxide of the product of Example 276 was prepared by treating 6-methanesulfonamido-3,4-dihydro-1'-[2-(2-chloro-pyrid-5-yl)ethyl]spiro [(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.170 g, 0.000378 mol) in 120 mL of chloroform with 0.276 g (0.0008 mol) of m-chloroperbenzoic acid at room temperature overnight. Calcium hydroxide (0.12 g, 0.0016 mol) was added, the mixture was stirred one hour at room temperature and was filtered and concentrated in vacuo. Flash chromatography on silica gel using CH2Cl2 :methanol:concentrated NH4OH (90:10:2) gave the title compound, mp 170°-171° C.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef652f456f9b42f9adc1127a03543f9a
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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