Water → HCID 19045659, compound

HRID 1781510Notes

Reaction equation

HRID 1781510 reaction equation
[F:1][C:2]([F:23])([F:22])[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][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=1)[CH2:11]2)=[O:4].[N+:24]([O-:27])([O-:26])=[O:25].[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C(Cl)(Cl)Cl>[F:23][C:2]([F:1])([F:22])[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+:24]([O-:26])=[O:25])=[C:15]([O:20][CH3:21])[CH:16]=1)[CH2:11]2)=[O:4].[F:23][C:2]([F:1])([F:22])[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][CH:14]=[C:15]([O:20][CH3:21])[C:16]=1[N+:24]([O-:27])=[O:25])[CH2:11]2)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 22985Ammonium nitrateHCID 19045751HCID 19045751, compound

Product 2

HCID 19045659HCID 19045659, compoundHCID 19045811HCID 19045811, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.0 g of 1'-trifluoroacetyl-3,4-dihydro-6-methoxyspiro[naphthalene-2(1H),2'-piperidine] was dissolved in 150 ml of chloroform. After 1.5 g of ammonium nitrate was suspended in this solution, 9 ml of trifluoroacetic anhydride was added, followed by overnight stirring at room temperature. After water was added, the reaction mixture was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate and filtered, after which the solvent was distilled off. The residue was purified by silica gel column chromatography to yield 1.4 g of 1'-trifluoroacetyl-3,4-dihydro-6-methoxy-7-nitrospiro[naphthalene-2(1H),2'-piperidine] and 0.457 g of 1'-trifluoroacetyl-3,4-dihydro-6-methoxy-5-nitrospiro[naphthalene-2(1H),2'-piperidine].

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4cc0c6f610bb40f9a1e1e4c513076ae5
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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