Amantadine → HCID 5302983, compound

HRID 2293108Notes

Reaction equation

HRID 2293108 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[C:17]12([NH2:27])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>>[C:17]12([NH:27][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N+:8]([O-:10])=[O:9])[CH2:24][CH:23]3[CH2:22][CH:21]([CH2:20][CH:19]([CH2:25]3)[CH2:18]1)[CH2:26]2

Participants

4

Reactant 3

HCID 2130AmantadineHCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 5302983HCID 5302983, compoundYield 62.8%

Procedure

A mixture of 2-chloronitrobenzene (10 g), potassium carbonate (17.5 g) copper (I) iodide (609 mg) and 1-adamantanamine (19.2 g) was heated at 180° under nitrogen for 6 h. The mixture was allowed to cool to room temperature and was adsorbed onto silica. This was chromatographed with hexane-EA (9:1) as eluent to give the title compound (10.86 g) as an orange/brown crystalline solid containing 29% 2-chloronitrobenzene. T.l.c. (99:1 hexane-EA) Rf 0.23

Workup

  1. temperaturewas heated at 180° under nitrogen for 6 h
  2. customThis was chromatographed with hexane-EA (9:1) as eluent

Sources & evidence

ORD record
ord-7c3a8ab779a24e268e9d1f7ed871cffd
Source dataset
uspto-grants-1997_11
Patent number
US05686449

Reaction notes

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