Potassium Carbonate → 6-(3-Piperidinomethylphenoxy)hexanenitrile

HRID 35593

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:6]1([CH2:5][C:4]2[CH:3]=[C:2]([CH:14]=[CH:13][CH:12]=2)[O:1][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

N-(3-Hydroxybenzyl)piperidine (9.55 g) was heated with 6-bromohexanenitrile (10.2 g) and potassium carbonate (13.8 g) under reflux in acetone (150 ml) for 66 hours. The reaction mixture was cooled and filtered. The solvent was removed by evaporation and the residue was heated with stirring at 100° C. for one hour to remove unreacted 6-bromohexanenitrile and to yield 6-(3-piperidinomethylphenoxy)hexanenitrile as an oil.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered
customThe solvent was removed by evaporation
temperaturethe residue was heated
customto remove unreacted 6-bromohexanenitrile

Sources & evidence

ORD record: ord-7da3d269d1874f798df02cc7c96fa40f
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04767769

Linked notes

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