Water → HCID 83806163, compound

HRID 493440Notes

Reaction equation

HRID 493440 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2(C(O)=O)[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C1(P([N:33]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.O.CCO[C:40](C)=[O:41]>C1(C)C=CC=CC=1>[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([N:33]=[C:40]=[O:41])[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 67528606HCID 67528606, compound

Product 1

HCID 83806163HCID 83806163, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(4-fluorophenyl)-1-methyl-4-piperidinecarboxylic acid hydrochloride (273 mg) was dissolved in dry toluene (10 mL) and, under a Nitrogen athmosphere and at r.t., TEA (0.33 mL) and diphenylphosphoryl azide (0.34 mL) were added. The mixture was refluxed for 4 h. Then water and AcOEt were added; the organic phase was separated and washed with brine, dried and evaporated under vacuum to give a crude which was purified by flash chromatography (elution with DCM:MeOH 9:1) to afford the title compound (47 mg) as white foam.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. customthe organic phase was separated
  3. washwashed with brine
  4. customdried
  5. customevaporated under vacuum
  6. customto give a crude which
  7. customwas purified by flash chromatography (elution with DCM:MeOH 9:1)

Sources & evidence

ORD record
ord-441cca0f88754d9fb01ddd1df0cf0a07
Source dataset
uspto-grants-2009_05
Patent number
US07534893B2

Reaction notes

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