Acetic Acid → HCID 59815626, compound

HRID 2117640Notes

Reaction equation

HRID 2117640 reaction equation
F[C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4](O)[CH:5]=[CH:6][C:7]=1[F:8].O[CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([CH3:20])[CH2:15]1.[H-].[Na+].[C:23](O)(=[O:25])C>C1COCC1.CO>[F:8][C:7]1[CH:2]=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=[CH:5][C:6]=1[O:25][CH2:23][CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([CH3:20])[CH2:15]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 980163-Piperidinol, 1-methyl-HCID 22112119HCID 22112119, compound

Product 1

HCID 59815626HCID 59815626, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Alternatively, the nitro derivative was prepared as follows: 3,4-Difluoronitro phenol (3 g, 18.7 mmol) and 3-hydroxy-1-methylpiperidine (2.5 g, 19.3 mmol) were dissolved in dry THF (100 mL) under nitrogen. Sodium hydride (60%, 1 g, 25 mmol) was slowly added under positive nitrogen pressure. The resulting light yellow solution was heated at 60° C. for 2.5 h. The dark-red solution was left to cool to room temperature and quenched with a solution of acetic acid (0.3 mL, 5.2 mmol) in methanol (10 mL). Solvent was removed under reduced pressure to yield an orange solid that was purified by column chromatography using DCM: MeOH (75: 25) as eluent to yield 3-(2-fluoro-4-nitro phenoxymethyl)-1-methylpiperidine as an orange oil.

Workup

  1. customAlternatively, the nitro derivative was prepared
  2. waitThe dark-red solution was left
  3. temperatureto cool to room temperature
  4. customSolvent was removed under reduced pressure
  5. customto yield an orange solid
  6. customthat was purified by column chromatography

Sources & evidence

ORD record
ord-cd59130de7f348e1884691bd7d5bd658
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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