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

HRID 1090114Notes

Reaction equation

HRID 1090114 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[CH:2][CH3:3].[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[N+:18]=[N-:19])=[CH:13][CH:12]=1>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:1]([N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:2]([CH3:3])[N:19]=[N:18]2)=[CH:13][CH:12]=1

Participants

3

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 30.5%

Procedure

1-(1-propenyl)-piperidine (9.4 g; 75.07 mmol) and 4-fluorophenylazide (10.3 g; 75.07 mmol), prepared as described in example 1, were admixed at 0° C. and the resultant mixture was kept at room temperature for 54 hours in the absence of light. The obtained solid mass was collected with petroleum ether and filtered obtaining the title compound (6 g). The mother liquor was evaporated and the resultant crude compound was purified by chromatography on silica gel (230-400 mesh), eluent petroleum ether:ethyl acetate=9:1, obtaining further title compound (m.p. 75° 76° C.).

Workup

  1. customwere admixed at 0° C.
  2. customThe obtained solid mass was collected with petroleum ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-62ca70e0b3a2422f8caaa317d2c841fc
Source dataset
uspto-grants-1992_01
Patent number
US05081136

Reaction notes

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