Piperidine → 4-Piperidinylbut-1-ene

Reaction equation

Br[CH2:2][CH2:3][CH:4]=[CH2:5].[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>>[N:6]1([CH2:7][CH2:8][CH:9]=[CH2:10])[CH2:11][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 8082Piperidine

HCID 21241Homoallyl bromide

Product 1

HCID 45622824-Piperidinylbut-1-eneYield 93.4%

Procedure

4-Bromobut-1-ene (1.35 g) was treated with piperidine (1.7 g) and heated at reflux for 3 hours. The mixture was cooled to ambient temperature, filtered and the residue washed with ether (50 mL). The combined filtrate and washings were evaporated to give the title compound (1.3 g).

Workup

temperatureheated
temperatureat reflux for 3 hours
filtrationfiltered
washthe residue washed with ether (50 mL)
customThe combined filtrate and washings were evaporated

Sources & evidence

ORD record: ord-d7ef957ab1cf46f68f1f4c42cdc7ceea
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087757B2

Reaction notes

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