Sodium Azide → HCID 18621467, compound

HRID 324541Notes

Reaction equation

HRID 324541 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C=O)C.O>[CH2:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][N:1]=[N+:2]=[N-:3])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86584029HCID 86584029, compound

Product 1

HCID 18621467HCID 18621467, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium azide was added to a solution of 4-benzyl-1-(3-p-toluenesulfonyloxypropyl)piperidine (0.216 g, 0.56 mmol) in DMF (5 mL). The resulting solution was stirred at 80° C. for 3 h then cooled at 25° C., diluted with water (50 mL) and extracted with diethyl ether (2×50 mL). The collected organic phase was washed with water (2×50 mL), dried and concentrated in vacuum to afford crude title compound as an oil (0.15 g). 1H-NMR (CDCl3): 1.2-1.4 (m, 2H), 1.4-1.6 (m, 1H) 1.628 (dd, J=13.2 Hz, 2H), 1. 761 (t, J=7.2 Hz, 2H), 1.857 (t, J=11.4 Hz, 2H), 2.367 (t, J=7.2 Hz, 2H), 2.53 (d, J=7.2 Hz, 2H), 2.86 (bd, J=11.4, 2H), 3.314 (t, J=6.9 Hz, 2H), 7.14 (d, J=7.5 Hz, 2H), 7.19 (d, J=6.9, 1H), 7.275 (t, J=7.2 Hz, 2H).

Workup

  1. temperaturethen cooled at 25° C.
  2. extractionextracted with diethyl ether (2×50 mL)
  3. washThe collected organic phase was washed with water (2×50 mL)
  4. customdried
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-64ae5d2695504ef1963704ecae51d3e7
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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