Amantadine → HCID 68469414, compound

HRID 502998Notes

Reaction equation

HRID 502998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:20])[C:10]([C:13]2([C:17]([OH:19])=O)[CH2:16][CH2:15][CH2:14]2)=[N:11][N:12]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[C:54]12([NH2:64])[CH2:63][CH:58]3[CH2:59][CH:60]([CH2:62][CH:56]([CH2:57]3)[CH2:55]1)[CH2:61]2>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[C:54]12([NH:64][C:17]([C:13]3([C:10]4[N:9]([CH3:20])[C:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])=[N:12][N:11]=4)[CH2:14][CH2:15][CH2:16]3)=[O:19])[CH2:61][CH:60]3[CH2:59][CH:58]([CH2:57][CH:56]([CH2:62]3)[CH2:55]1)[CH2:63]2

Participants

7

Reactant 4

HCID 2130AmantadineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 68466046HCID 68466046, compound

Product 1

HCID 68469414HCID 68469414, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-[5-(2-Chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]cyclobutanecarboxylic acid (200 mg) was suspended in methylene chloride (7 ml) and then diisopropylethylamine (0.72 ml) and bromotris(pyrrolidino)phosphonium hexafluorophosphate salt (416 mg) were added thereto, followed by stirring at room temperature for 30 minutes. Then, 1-adamantanamine (104 mg) was added to the reaction solution and the whole was stirred at room temperature for 15 hours. The reaction solution was diluted with a saturated aqueous sodium bicarbonate solution (30 ml), followed by extraction with chloroform (20 ml×2). The organic layer was dried over anhydrous sodium sulfate and filtrated and then the solvent was removed by evaporation under reduced pressure. The resulting residue was purified by column chromatography (methanol:chloroform=2:98) and the resulting solid washed with hexane and diethyl ether to obtain 212 mg of N-1-adamantyl-1-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]cyclobutanecarboxamide (white solid).

Workup

  1. stirringthe whole was stirred at room temperature for 15 hours
  2. extractionfollowed by extraction with chloroform (20 ml×2)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe resulting residue was purified by column chromatography (methanol:chloroform=2:98)
  7. washthe resulting solid washed with hexane and diethyl ether

Sources & evidence

ORD record
ord-2e80c2d0aca6479f9b32938c98f950b8
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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