Nitric Acid → HCID 19791111, compound

HRID 1655198Notes

Reaction equation

HRID 1655198 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:40])[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)=[N:17][CH:16]=1.[N+:41]([O-])([OH:43])=[O:42].C(OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[O:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:40])[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([CH:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:23][CH2:22]2)=[N:17][CH:16]=1)[N+:41]([O-:43])=[O:42]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 19791099HCID 19791099, compound

Product 1

HCID 19791111HCID 19791111, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.66 g of N-(11-hydroxy-1-undecanyl)-6-(4-diphenylmethyl-1-piperazinyl)nicotinamide were dissolved in 15 ml of methylene chloride and to the solution was added dropwise under ice-cooling a mixed solution of 0.2 ml of fuming nitric acid and 0.5 ml of acetic anhydride and stirred for 6 hrs. This reaction mixture was poured into an aqueous sodium hydrogencarbonate solution, extracted with methylene chloride, washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 0.41 g (57%) of the title compound.

Workup

  1. additionwas added dropwise under ice-
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-26a91e109d524a7f8064f84d84fac05d
Source dataset
uspto-grants-1993_10
Patent number
US05250526

Reaction notes

Loading…