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

HRID 1193400Notes

Reaction equation

HRID 1193400 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 91%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1,4-Dioxa-8-azaspiro[4.5]decane (5.0 g, 34.9 mmol, 1.0 eq.), 4-bromopyridine HCl (7.46 g, 38.46 mmol, 1.1 eq.) and DIPEA (18.2 ml, 104.7 mmol, 3.0 eq.) were dissolved in n-butanol (100 ml) and refluxed for 36 hours. The reaction solution was concentrated under reduced pressure and purified by column chromatography (Alox, 3% MeOH in DCM). Yield: 91% (7.0 g, 31.81 mmol)

Workup

  1. temperaturerefluxed for 36 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. custompurified by column chromatography (Alox, 3% MeOH in DCM)

Sources & evidence

ORD record
ord-0e4511ee966c4e0f86c47538cc1ac80f
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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