Amantadine → HCID 86681267, compound

HRID 336599Notes

Reaction equation

HRID 336599 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-62c3ae8c56ff4446b7cd609812d1818c
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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