Nitromethane → HCID 19883424, compound

HRID 344673Notes

Reaction equation

HRID 344673 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.[O-]CC.[Na+].[N+:14]([CH3:17])([O-:16])=[O:15].Cl.C(O)(C)C>C1(C)C=CC=CC=1.C(O)C>[N+:14]([CH2:17][C:3]1([OH:9])[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 195073-QuinuclidinoneHCID 2723922Sodium ethoxideHCID 21912024Isopropanol hydrochloride

Product 1

HCID 19883424HCID 19883424, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Quinuclidin-3-one (125 g., 1 mole) was dried by azeotropic distillation (40% w/w in toluene) and placed in a 3 l. flask equipped with a mechanical stirrer, 1 l. methanolic sodium ethoxide was added and the clear solution was stirred at 15°-20° C. Nitromethane, 61 g. (1.0 mole), dissolved in 500 ml. absolute ethanol was then added over 0.5 hour while keeping the temperature below 20° C. The solution was acidified to pH=1 using HCl-isopropanol, filtered and dried to yield 160 g. crude product which was used as such for the next step.

Workup

  1. customflask equipped with a mechanical stirrer
  2. dissolution(1.0 mole), dissolved in 500 ml
  3. customthe temperature below 20° C
  4. filtrationfiltered
  5. customdried
  6. customto yield 160 g

Sources & evidence

ORD record
ord-9d82a6f89c81441999cc19c012520bac
Source dataset
uspto-grants-1991_10
Patent number
US05053412

Reaction notes

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