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

HRID 1291912Notes

Reaction equation

HRID 1291912 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.Cl[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CC(C)C>[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 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 818524-Chloropyridine hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 1,4-dioxa-8-azaspiro[4,5]decane (51.2 ml), 4-chloropyridine hydrochloride (20 g) and potassium carbonate (18.4 g) in isoamyl alcohol (400 ml) was gently refluxed for 18 hr. The reaction mixture was cooled and filtered. The filtrate was evaporated to give a waxy solid which was triturated with hexane to give 8-(4-pyridyl)-1,4-dioxa-8-azaspiro[4,5]decane (24.16 g) as a colourless solid; NMR (d6 -DMSO) δ 1.65-1.70 (4H, m), 3.45-3.55 (4H, m), 3.9 (4H, s), 6.90 (2H, m), 8.15 (2H, m); m/Z 221 (M+H)+.

Workup

  1. temperaturewas gently refluxed for 18 hr
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customto give a waxy solid which
  6. customwas triturated with hexane

Sources & evidence

ORD record
ord-f3ddfd84f519482ba98a2cef8f0c96df
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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