Potassium Carbonate → (RS)-1-Benzyl-2-[5-(4-fluoro-phenyl)-tetrazol-2-ylmethyl]-piperidine

HRID 30183Notes

Reaction equation

HRID 30183 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[N:25][NH:26][N:27]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C>C1(C)C(C)=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][N:25]1[N:26]=[N:27][C:23]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[N:24]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 7661405-(4-Fluorophenyl)-1H-tetrazoleHCID 231462741-Benzyl-2-(bromomethyl)piperidine

Product 1

HCID 67158567(RS)-1-Benzyl-2-[5-(4-fluoro-phenyl)-tetrazol-2-ylmethyl]-piperidine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-Benzyl-2-bromomethylpiperidine (2.1 g), 5-(4-fluoro-phenyl)-2H-tetrazole (1.28 g) and potassium carbonate (6 g) were combined in xylene (100 ml) containing diisopropylethylamine (7 ml) and boiled for 16 h. The reaction mixture was cooled to room temperature, filtered, solvent removed at reduced pressure and the residue column chromatographed (silica gel; diethyl ether/petroleum ether 40:60 eluant) to give after combining appropriate fractions and removing solvent at reduced pressure the title compound 1.44 g.

Workup

  1. filtrationfiltered
  2. customsolvent removed at reduced pressure
  3. customthe residue column chromatographed (silica gel; diethyl ether/petroleum ether 40:60 eluant)
  4. customto give
  5. customremoving solvent at reduced pressure the title compound 1.44 g

Sources & evidence

ORD record
ord-80719b014c79452da8249384f88afc28
Source dataset
uspto-grants-2008_09
Patent number
US07423052B2

Reaction notes

Loading…