4-Nitrobenzoyl chloride → 2-Acetoxy-5-(1-benzylpiperidin-4-yl)-1-(4-nitrobenzoyloxyimino)pentylamine

HRID 54557Notes

Reaction equation

HRID 54557 reaction equation
[C:1]([O:4][CH:5]([CH2:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)[C:6]([NH2:9])=[N:7][OH:8])(=[O:3])[CH3:2].[N+:26]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)([O-:28])=[O:27]>O1CCCC1>[C:1]([O:4][CH:5]([CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:17][CH2:18]1)[C:6]([NH2:9])=[N:7][O:8][C:33](=[O:34])[C:32]1[CH:31]=[CH:30][C:29]([N+:26]([O-:28])=[O:27])=[CH:37][CH:36]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 539686962-Acetoxy-5-(1-benzylpiperidin-4-yl)-1-hydroxyiminopentylamine

Product 1

HCID 540644882-Acetoxy-5-(1-benzylpiperidin-4-yl)-1-(4-nitrobenzoyloxyimino)pentylamineYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-acetoxy-5-(1-benzylpiperidin-4-yl)-1-hydroxyiminopentylamine (0.59 g) in tetrahydrofuran (5 ml) was added dropwise to a solution of 4-nitrobenzoyl chloride (0.29 g) in tetrahydrofuran (5 ml) and the mixture was stirred overnight at ambient temperature and extracted with ethyl acetate. The extract was washed with a sodium hydrogencarbonate aqueous solution and water, dried over magnesium sulfate and evaporated in vacuo to give 2-acetoxy-5-(1-benzylpiperidin-4-yl)-1-(4-nitrobenzoyloxyimino)pentylamine (0.35 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a sodium hydrogencarbonate aqueous solution and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-50a296be11a14b0b84e08e41c6f5d570
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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