1-Bromo-3-chloropropane → 2-[1-(3-Chloropropyl)piperidin-4-yl]ethan-1-ol

HRID 272825Notes

Reaction equation

HRID 272825 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[OH-].[Na+].Br[CH2:13][CH2:14][CH2:15][Cl:16]>CC(C)=O>[Cl:16][CH2:15][CH2:14][CH2:13][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 739534-Piperidineethanol

Product 1

HCID 404243272-[1-(3-Chloropropyl)piperidin-4-yl]ethan-1-olYield 38.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Piperidine ethanol (0.9 g, 7.5 mmol), acetone (18 ml, 20 vol), 5M NaOH solution (1.8 ml) and 1-bromo-3-chloropropane (3.54 g, 22.5 mmol, 3 eq.) were reacted together according to general procedure A to give the title compound (0.6 g, 37%) as an orange oil.

Sources & evidence

ORD record
ord-f30698aad9a04b93bb42b5650c55795a
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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