Amantadine → N-Adamantan-1-yl-phthalamic acid

HRID 435141Notes

Reaction equation

HRID 435141 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH2:12]1[CH:17]2[CH2:18][C:19]3([NH2:22])[CH2:21][CH:15]([CH2:16]2)[CH2:14][CH:13]1[CH2:20]3>C1(C)C=CC=CC=1>[C:19]12([NH:22][C:4](=[O:5])[C:3]3[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:1]([OH:6])=[O:11])[CH2:20][CH:13]3[CH2:14][CH:15]([CH2:16][CH:17]([CH2:12]3)[CH2:18]1)[CH2:21]2

Participants

4

Reactant 2

HCID 2130AmantadineHCID 6811Phthalic Anhydride

Product 1

HCID 2769946N-Adamantan-1-yl-phthalamic acidYield 96.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 25 g (0.17 mole) of phthalic anhydride and 100 ml of toluene was prepared. To this mixture was added a solution of approximately 25.5 g (0.17 mole) of adamantamine in 100 ml of toluene. The resulting mixture was stirred at room temperature for 15 hours. The solid was collected by vacuum filtration and dried in a vacuum oven at room temperature to yield approximately 49 g of N-adamantylphthalamic acid.

Workup

  1. customwas prepared
  2. filtrationThe solid was collected by vacuum filtration
  3. customdried in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-1a4ae662a9a548eaa0036fd6f8659e77
Source dataset
uspto-grants-1983_08
Patent number
US04400461

Reaction notes

Loading…