Amantadine → HCID 58928298, compound

HRID 852191Notes

Reaction equation

HRID 852191 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]4[CH2:19][O:18]4)=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[C:22]12([NH2:32])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2>C(O)C>[C:22]12([NH:32][CH2:19][C@@H:17]([OH:18])[CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([C:6]4[C:5]5[CH:20]=[CH:21][C:2]([F:1])=[CH:3][C:4]=5[O:8][N:7]=4)=[CH:10][CH:11]=3)[CH2:29][CH:28]3[CH2:27][CH:26]([CH2:25][CH:24]([CH2:30]3)[CH2:23]1)[CH2:31]2

Participants

4

Reactant 2

HCID 2130AmantadineHCID 58928269(R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole

Product 1

HCID 58928298HCID 58928298, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine (R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole (29) (250 mg, 0.86 mmol), 1-adamantanamine (530 mg, 3.50 mmol), ethanol (4.0 ml) and heat (˜80° C.) for 16 hours. Cool reaction to room temperature and concentrate (in vacuo). Purify the compound by column chromatography (silica) eluting with 28% aqueous ammonia/ethanol/chloroform (1:19:180) to obtain a white solid. Dry (50° C. at 0.5 mm Hg) to give 332 mg (86% yield) of the title compound. Purity by LC/MS=92%, [M+H]+=437.

Workup

  1. temperatureCool
  2. customreaction to room temperature
  3. concentrationconcentrate (in vacuo)
  4. customPurify the compound by column chromatography (silica)
  5. washeluting with 28% aqueous ammonia/ethanol/chloroform (1:19:180)
  6. customto obtain a white solid
  7. customDry (50° C. at 0.5 mm Hg)

Sources & evidence

ORD record
ord-e7c031e0cf5e41b4a7e0dffc2329555a
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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