m-Chloroperbenzoic acid → Ammonia

HRID 2243824Notes

Reaction equation

HRID 2243824 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]([C:12]1[O:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])=[CH:19][CH:18]=3)=[CH:14][CH:13]=1)=[O:11])[CH2:3][CH2:2]2.ClC1C=C(C=CC=1)C(OO)=[O:33]>ClCCl>[NH3:1].[N:1]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[N:4]([C:10]([C:12]1[O:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH+:23]([O-:33])[C:24](=[O:27])[CH:25]=[CH2:26])=[CH:19][CH:18]=3)=[CH:14][CH:13]=1)=[O:11])[CH2:3][CH2:2]2

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10067407HCID 10067407, compound

Product 2

HCID 222AmmoniaHCID 86606177HCID 86606177, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-{4-[5-(1,4-Diaza-bicyclo[3.2.2]nonane-4-carbonyl)-furan-2-yl]-phenyl}-acrylamide (175 mg; 0.479 mmol), m-chloroperoxybenzoic acid (165 mg; 0.958 mmol) and dichloromethane (5 ml) was stirred at room-temperature for 15 hours. The crude mixture was evaporated. Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 180 mg (99%). Mp. 162° C.

Workup

  1. customThe crude mixture was evaporated

Sources & evidence

ORD record
ord-99d3d129a8074aed8de23a104e68efe0
Source dataset
uspto-grants-2010_03
Patent number
US07678788B2

Reaction notes

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