Sodium Azide → HCID 59438450, compound

HRID 2177473Notes

Reaction equation

HRID 2177473 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13](O)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>FC(F)(F)C(O)=O.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([N:24]=[N+:25]=[N-:26])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 59438410Benzyl 3-hydroxy-3-phenylpiperidine-1-carboxylate

Product 1

HCID 59438450HCID 59438450, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

g (3.212 mmol) 3-Hydroxy-3-phenyl-piperidine-1-carboxylic acid benzyl ester was dissolved in a cold mixture (10° C.) of trifluoroacetic acid (12.3 ml) and water (2.0 ml). The solution was cooled to 0° C. and 1.46 g (22.48 mmol) sodium azide were added portionwise. The temperature rose to 10° C. The ice bath was removed and the mixture was stirred at room temperature for 3 hours. The mixture was cooled in an ice bath and basified by dropwise addition of a 25% ammonium hydroxide solution (13.0 ml) maintaining the temperature below 20° C. The mixture was diluted with water (45 ml) and extracted 3 times with dichloromethane. The combined extracts were washed once with brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide the title compound as a light yellow oil which was used in the next step without further purification.

Workup

  1. customrose to 10° C
  2. customThe ice bath was removed
  3. temperatureThe mixture was cooled in an ice bath
  4. additionbasified by dropwise addition of a 25% ammonium hydroxide solution (13.0 ml)
  5. temperaturemaintaining the temperature below 20° C
  6. additionThe mixture was diluted with water (45 ml)
  7. extractionextracted 3 times with dichloromethane
  8. washThe combined extracts were washed once with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-140564a3961b4104a10188e659ed05be
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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