N-(1-propenyl)piperidine → 1-(4-Fluorophenyl)-4-methyl-5-piperidino-4,5-dihydro-1,2,3-triazole

HRID 1258905Notes

Reaction equation

HRID 1258905 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH:11]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[CH:12][CH3:13]>CCCCCC>[F:10][C:7]1[CH:8]=[CH:9][C:4]([N:1]2[CH:11]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:12]([CH3:13])[N:3]=[N:2]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 138954N-(1-propenyl)piperidineHCID 108879741-Azido-4-fluorobenzene

Product 1

HCID 199146541-(4-Fluorophenyl)-4-methyl-5-piperidino-4,5-dihydro-1,2,3-triazoleYield 21%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Prepared in analogy to EP 0 433 842 A2. A mixture of 1-azido-4-fluoro-benzene (2.80 g, 20 mmol) and 1-(1-propenyl)-piperidine (18%, 14.2 g, 20 mmol) was stirred under ice cooling (slowly exothermic in the beginning) and at room temperature for 144 h in the absence of light. Hexane was then added to the brown solutions and a solid formed which was filtered off, washed with hexane and dried in hv to give the title product (1.1 g) as a light pink solid. The filtrate was then evaporated and purification by chromatography (silica, 10 to 50% ethyl acetate in heptane) afforded the title compound (4.34 g) as a light yellow solid. Total yield (5.44 g, 98%). MS: m/e=263.1 [M+H]+.

Workup

  1. customa solid formed which
  2. filtrationwas filtered off
  3. washwashed with hexane
  4. customdried in hv

Sources & evidence

ORD record
ord-120e710419d84b10844ad92eac4372e4
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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