Amantadine → HCID 86681267, compound

HRID 588676Notes

Reaction equation

HRID 588676 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:13]12([NH2:23])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.C(N(C(C)C)CC)(C)C>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([NH:23][C:13]23[CH2:14][CH:15]4[CH2:21][CH:19]([CH2:18][CH:17]([CH2:16]4)[CH2:22]2)[CH2:20]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 2130AmantadineHCID 81531DiisopropylethylamineHCID 446310013-Bromo-2-methylbenzene-1-sulfonyl chloride

Product 1

HCID 86681267HCID 86681267, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-2-methylbenzene-1-sulfonyl chloride (300 mg) and 1-adamantanamine (185 mg) were dissolved in dichloromethane (4 mL). Diisopropylethylamine (432 mg) was added, and the solution was stirred at room temperature for 16 hours. The solution was diluted with 70% ethyl acetate (hexanes), washed three times with 1 M aqueous HCl, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed to yield the product.

Workup

  1. washwashed three times with 1 M aqueous HCl
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was removed
  6. customto yield the product

Sources & evidence

ORD record
ord-cf6bfd78f835410484a3bebcdb9c8fbe
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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