Phosphorus pentachloride → 1-Benzyl-4-(1-methyl-1H-tetrazol-5-YL)piperidine

HRID 403508Notes

Reaction equation

HRID 403508 reaction equation
[CH3:1][NH:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.C[Si]([N:28]=[N+:29]=[N-:30])(C)C>ClCCl>[CH2:11]([N:8]1[CH2:9][CH2:10][CH:5]([C:3]2[N:2]([CH3:1])[N:30]=[N:29][N:28]=2)[CH2:6][CH2:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 78378AzidotrimethylsilaneHCID 409218631-benzyl-N-methylpiperidine-4-carboxamide

Product 1

HCID 683791341-Benzyl-4-(1-methyl-1H-tetrazol-5-YL)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-benzyl-piperidine-4-carboxylic acid methylamide (36) (853 mg, 3.67 mmol) in dichloromethane (10 ml) was cooled in an ice-bath and phosphorous pentachloride (841 mg, 4 mmol) was added dropwise. The mixture was stirred at rt for 5 h, cooled to −5° C. and trimethylsilyl azide (387 ul, 3.67 mmol) was added dropwise. The reaction mixture was stirred for 3 h at rt and was then quenched by addition of sat. aqueous NaHCO3 solution. The organic layer was washed with water and brine, dried over Na2 SO4 and evaporated to yield a colorless solid.

Workup

  1. temperaturecooled to −5° C.
  2. stirringThe reaction mixture was stirred for 3 h at rt
  3. customwas then quenched by addition of sat. aqueous NaHCO3 solution
  4. washThe organic layer was washed with water and brine
  5. customdried over Na2 SO4
  6. customevaporated
  7. customto yield a colorless solid

Sources & evidence

ORD record
ord-30ebac957e704806a67149246672af97
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

Loading…