Amantadine → HCID 23626599, compound

HRID 1459395Notes

Reaction equation

HRID 1459395 reaction equation
[C:1]12([NH2:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.[Br:19][CH2:20][C:21](Br)=[O:22]>C1(C)C=CC=CC=1>[C:1]12([NH:11][C:21](=[O:22])[CH2:20][Br:19])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 2130AmantadineHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 23626599HCID 23626599, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an anhydrous toluene solution (25 ml) at 0° C. containing 1-adamantanamine (4.445 g, 29.39 mmol) and triethylamine (4.92 ml, 35.27 mmol) under a nitrogen atmosphere was added dropwise with strirring a solution of bromoacetyl bromide (2.56 ml, 29.39 mmol in 10 ml of toluene). The solution was warmed to ambient temperature and stirred for 2.5 hours. The triethylamine (TEA) salts were filtered and washed with toluene. The filtrate was extracted with 1 M HCl and brine, dried (Na2SO4) and concentrated in vacuo to yield 5.74 g (71%) of the title compound as a light brown solid which was crystallized from ether/hexane.

Workup

  1. additionwas added dropwise
  2. filtrationThe triethylamine (TEA) salts were filtered
  3. washwashed with toluene
  4. extractionThe filtrate was extracted with 1 M HCl and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-777858ee91d648479edd02ec5d503e89
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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