Acetic Acid → HCID 53819161, compound

HRID 361837Notes

Reaction equation

HRID 361837 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[N+:22]([O-])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].[CH3:28][C:29]([CH3:31])=O.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.CO.[OH-].[Na+].[Pt]=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[NH:22][CH:29]([CH3:31])[CH3:28])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 180Acetone2×HCID 5003444Sodium cyanoborohydride2×HCID 53836267HCID 53836267, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53819161HCID 53819161, compound

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1 Benzyl-4-[N-methyl-N-(2-nitro-4-fluorophenyl)amino]piperidine (EXAMPLE 169, 3.0, 8.73 mmol) and platinum oxide (1.5 g) in 100 ml ethanol is hydrogenated under 69 kPa (10 psi) hydrogen for one hr. Filtration and evaporation of the solvent gives a product which is dissolved in methanol (0.2M) and cooled to 0°. Acetone (0.71 ml, 9.60 mmol) and acetic acid (5.0 ml, 87.3 mmol) is added. After 10 minutes of stirring, sodium cyanoborohydride (628 mg, 9.25 mmol) is added and the mixture warmed to 20°-25°. Twice more the mixture is cooled to 0° and acetone (9.60 mmol) and sodium cyanoborohydride (9.25 mmol) are added, warming to 20°-25° each time. The mixture is diluted with sodium hydroxide (1N) and extracted with chloroform. The extract is dried over sodium sulfate, filtered, and evaporated to give the tide compound, NMR (300 MHz, CD3OD) 7.29, 7.0, 6.30, 6.22, 3.55, 3.47, 2.95, 2.70, 2.50, 2.0, 1.50 and 1.18δ.

Workup

  1. filtrationFiltration and evaporation of the solvent
  2. customgives a product which
  3. temperaturecooled to 0°
  4. temperaturethe mixture warmed to 20°-25°
  5. temperatureTwice more the mixture is cooled to 0°
  6. temperaturewarming to 20°-25° each time
  7. extractionextracted with chloroform
  8. dry with materialThe extract is dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto give the tide compound, NMR (300 MHz, CD3OD) 7.29, 7.0, 6.30, 6.22, 3.55, 3.47, 2.95, 2.70, 2.50, 2.0, 1.50 and 1

Sources & evidence

ORD record
ord-cd17673914f8433dbe00dce8e1959643
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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