Cyclohexene oxide → 8-(2-Oxo-cyclohexyl)-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one

HRID 347311Notes

Reaction equation

HRID 347311 reaction equation
[C:1]1([CH:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]12[O:24][CH:23]1[CH2:22][CH2:21][CH2:20][CH2:19]2>C(O)C>[O:24]=[C:23]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[N:14]1[CH2:13][CH2:12][C:11]2([C:10](=[O:17])[NH:9][CH2:8][CH:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 9246Cyclohexene oxideHCID 127097244-Phenyl-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 210825658-(2-Oxo-cyclohexyl)-4-phenyl-2,8-diaza-spiro[4.5]decan-1-oneYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of rac-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one (13.10 g, 56.9 mmol) and 7-oxa-bicyclo[4.1.0]heptane (5.58 g, 56.9 mmol) in ethanol (250 mL) was heated under reflux for 3 days. After cooling to room temperature the mixture was filtered and the filtrate evaporated to afford the title compound (18.14 g, 97%) which was obtained as off-white solid. MS: m/e=329.3 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. filtrationwas filtered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-898ada5d43f24a40a17a70f4063f2e6b
Source dataset
uspto-grants-2007_02
Patent number
US07173133B2

Reaction notes

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