1,4-Dioxa-8-azaspiro(4.5)decane → 8-(Pyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1193304Notes

Reaction equation

HRID 1193304 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl.Br[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>C(O)CCC>[N:16]1[CH:17]=[CH:18][C:13]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 81531DiisopropylethylamineHCID 881004-Bromopyridinium chloride

Product 1

HCID 153824168-(Pyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 58%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1,4-Dioxa-8-azaspiro[4.5]decane (10.0 g, 69.9 mmol, 1 eq) and 4-bromopyridine hydrochloride (16.2 g, 83.7 mmol, 1.2 eq) were dissolved in n-butanol (120 ml) and DIPEA (23 ml, 139.8 mmol, 2 eq) and refluxed for 14 h. After monitoring by thin-layer chromatography, the reaction solution was concentrated under reduced pressure. After purification by column chromatography (silica gel, 3% MeOH in dichloromethane), the desired product was obtained in the form of a white solid. Yield: 58% (9.0 g, 40.9 mmol).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customAfter purification by column chromatography (silica gel, 3% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-65eba4947dba4d7bbb605a81e3c40773
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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