1,4-Dioxa-8-azaspiro(4.5)decane → HCID 57024242, compound

HRID 1418373Notes

Reaction equation

HRID 1418373 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)=[O:7].[CH2:13]1[O:22][C:16]2(CCNC[CH2:17]2)[O:15][CH2:14]1>C1COCC1>[CH2:13]1[O:22][C:16]2([CH2:17][CH2:9][N:8]([C:6]([C:2]3[NH:1][CH:5]=[CH:4][CH:3]=3)=[O:7])[CH2:12][CH2:11]2)[O:15][CH2:14]1

Participants

4

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 45084590HCID 45084590, compound

Product 1

HCID 57024242HCID 57024242, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(1H-pyrrole-2-carbonyl)imidazole (0.54 g, 3.4 mnmol) and 4-piperidone ethylene ketal (0.43 ml, 3.4 mmol) in THF (10 ml) was heated at reflux for 1 h. The mixture was cooled and evaporated, diluted with ethyl acetate, washed with dilute HCl, dried over sodium sulphate and evaporated to afford a beige solid (0.56 g), MS (+CI) 237 ([M+H]+), 1H NMR (CDCl3) 9.47 (1H, br. s), 6.92 (1H, m), 6.53 (1H, m), 6.25 (1H, m), 4.00 (4H, s), 3.91 (4H, t, J 5.4 Hz), 1.78 (4H, t, J 5.8 Hz).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe mixture was cooled
  3. customevaporated
  4. additiondiluted with ethyl acetate
  5. washwashed with dilute HCl
  6. dry with materialdried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-33ab5a5a0e9f4c72b201ca2861ce0e89
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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