1-Bromo-3-chloropropane → 1-(3-Chloropropyl)piperidin-4-ol

HRID 272821Notes

Reaction equation

HRID 272821 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[OH-].[Na+].Br[CH2:11][CH2:12][CH2:13][Cl:14]>CC(C)=O>[Cl:14][CH2:13][CH2:12][CH2:11][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 79341Piperidin-4-ol

Product 1

HCID 127257181-(3-Chloropropyl)piperidin-4-olYield 28.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Hydroxypiperidine (3 g, 30 mmol), acetone (60 ml, 20 vol), 5M NaOH solution (7.2 ml) and 1-bromo-3-chloropropane (14.2 g, 90 mmol, 3 eq.) were reacted together according to general procedure A to give the title compound (1.5 g, 28%) as a pale yellow oil.

Sources & evidence

ORD record
ord-762830318ee346abb9143938fe39e480
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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