Sodium Hydroxide → HCID 14987156, compound

HRID 2051518Notes

Reaction equation

HRID 2051518 reaction equation
COC([N:5]1[CH2:10][CH2:9][C@H:8]([N:11](C(=O)CC)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[C@H:7]([CH3:23])[CH2:6]1)=O.[OH-].[Na+]>Br>[CH3:23][C@H:7]1[C@@H:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:9][CH2:10][NH:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14987155HCID 14987155, compound

Product 1

HCID 14987156HCID 14987156, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of cis-1-methoxycarbonyl-3-methyl-4-[(1-oxo-propyl)-2-fluorophenylamino]-piperidine (3.2 g, 9.89 mmol) in 48% aqueous HBr (20 ml) is refluxed for two hours. Upon heating the mixture dissolution occurs. The solution is cooled to 0° C. and 5N NaOH is added until the pH is between 11 and 12. The aqueous phase is extracted with methylene chloride (5×) and the combined organics dried over sodium sulfate and concentrated to give cis-3-methyl-4-(2-fluorophenylamino)-piperidine as an oil: 2.0 g; 97%.

Workup

  1. temperatureis refluxed for two hours
  2. temperatureUpon heating
  3. dissolutionthe mixture dissolution
  4. extractionThe aqueous phase is extracted with methylene chloride (5×)
  5. dry with materialthe combined organics dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-727298684b4b44fca66d0e4f9ad708dd
Source dataset
uspto-grants-1991_05
Patent number
US05019583

Reaction notes

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