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

HRID 549344Notes

Reaction equation

HRID 549344 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 10.44 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 10.44 g

Sources & evidence

ORD record
ord-927f57ebbb234062a58014eabdeae23e
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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