1,5-Dibromopentane → 1-(4-Bromo-2,6-diethylbenzyl)-piperidine

HRID 1505886Notes

Reaction equation

HRID 1505886 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([CH2:10][CH3:11])[C:5]([CH2:6][NH2:7])=[C:4]([CH2:12][CH3:13])[CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][CH3:13])[C:5]([CH2:6][N:7]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH2:10][CH3:11])[CH:9]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 582667344-Bromo-2,6-diethylbenzylamine

Product 1

HCID 582665871-(4-Bromo-2,6-diethylbenzyl)-piperidineYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-2,6-diethylbenzylamine (90 mg, 0.37 mmol), 1,5-dibromopentane (56 μL, 0.41 mmol) and potassium carbonate (206 mg, 1.5 mmol) were suspended in dioxane (5 mL) and heated at 100° C. overnight. The reaction mixture was then cooled to ambient temperature, the solid removed by filtration and the filtrate concentrated in vacuo to afford an orange oil. The resultant oil was purified by flash chromatography (silica, 12 g column, ISCO, 0-10% methanol in DCM) to afford the title compound as yellow oil (66 mg, 58%). NMR (CDCl3, 300 MHz): 7.16 (s, 2H), 3.38 (s, 2H), 2.80-2.62 (m, 4H), 2.35 (s, 4H), 1.54-1.34 (m, 6H), 1.27-1.13 (m, 6H).

Workup

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. customthe solid removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customto afford an orange oil
  5. customThe resultant oil was purified by flash chromatography (silica, 12 g column, ISCO, 0-10% methanol in DCM)

Sources & evidence

ORD record
ord-3da36ac477b843a28ff68a0fd6a858ce
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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