Hydrochloric Acid → HCID 23361185, compound

HRID 232890Notes

Reaction equation

HRID 232890 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]21[CH2:19][CH2:18][C:17]1[C:12](=[CH:13][C:14]([N+:20]([O-])=O)=[CH:15][CH:16]=1)[C:11]2=[O:23])=[O:4].[ClH:26]>C(O)C.[C].[Pd]>[ClH:26].[NH2:20][C:14]1[CH:13]=[C:12]2[C:17]([CH2:18][CH2:19][C:6]3([C:11]2=[O:23])[CH2:7][CH2:8][CH2:9][CH2:10][N:5]3[C:3](=[O:4])[C:2]([F:25])([F:1])[F:24])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23361122HCID 23361122, compound

Product 1

HCID 23361185HCID 23361185, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.0 g of 1'-trifluoroacetyl-3,4-dihydro-7-nitrospiro[naphthalene-2(1H),2'-piperidine]-1-one in 50 ml of ethanol, 0.30 g of 10% palladium-carbon catalyst and 2 ml of concentrate hydrochloric acid were added, followed by 3 hours of catalytic reduction at normal pressure and temperature. After the catalyst was filtered off, the filtrate was distilled to remove the solvent. The residue was dissolved in methylene chloride and washed with water. The methylene chloride layer was dried over anhydrous magnesium sulfate and filtered, after which the solvent was distilled off. The residue was treated with 2.2 ml of 4 N-methanolic hydrochloric acid to yield a solid, which was then recrystallized from ethanol-ether to yield 2.37 g of 7-amino-1'-trifluoroacetyl-3,4-dihydrospiro[naphthalene-2(1H),2'-piperidine]-1-one hydrochloride as a white crystal.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. distillationthe filtrate was distilled
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationafter which the solvent was distilled off
  9. additionThe residue was treated with 2.2 ml of 4 N-methanolic hydrochloric acid
  10. customto yield a solid, which
  11. customwas then recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-b8cfe76311324f1882ae50e184b46174
Source dataset
uspto-grants-1997_01
Patent number
US05591849

Reaction notes

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