Potassium Carbonate → Decane

HRID 1290553Notes

Reaction equation

HRID 1290553 reaction equation
O1[C:5]2([CH2:10][CH2:9]N[CH2:7][CH2:6]2)OCC1.Cl.Cl[C:13]1[CH:18]=[CH:17]N=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CC(C)C>[CH3:15][CH2:14][CH2:13][CH2:18][CH2:17][CH2:9][CH2:10][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 15600Decane

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 reation 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 (d6DMSO) 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 reation 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-bf0822328e9b4c95b60bc0919cc03ed7
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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