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Amantadine → 2-(2-(1-Adamantylamino)anilin-5-yl)benzoxazole

HRID 74205
Notes
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Reaction equation

HRID 74205 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.C(=O)([O-])O.[Na+].[C:25]12([NH2:35])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.[H][H]>C(O)C.[C].[Pd].O1CCCC1.O>[C:25]12([NH:35][C:2]3[CH:7]=[CH:6][C:5]([C:8]4[O:9][C:10]5[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=5[N:12]=4)=[CH:4][C:3]=3[NH2:17])[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 2130AmantadineHCID 516892Sodium BicarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674988422-(2-(1-Adamantylamino)anilin-5-yl)benzoxazoleYield 16.1%

Reagents, catalysts & solvents 4

HCID 178418390
HCID 178418390, compound
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added sodium hydrogen carbonate (195 mg, 2.32 mmol) and 1-adamantylamine (185 mg, 1.22 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered off, washed with water and then dried. The crystals obtained were added to a tetrahydrofuran (5 mL) solution containing 10% palladium-carbon (100 mg), a hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 6 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (67.0 mg, 16% yield) as brown crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux
  3. filtrationthe precipitated crystals were filtered off
  4. washwashed with water
  5. customdried
  6. customThe crystals obtained
  7. stirringthis was stirred at room temperature for 6 hours
  8. filtrationthis was filtered through Celite
  9. concentrationthe filtrate was concentrated
  10. customThe residue obtained
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-017b0ca703ea443186c20c805724ba80
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829035B2

Reaction notes

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