4-Methylmorpholine → 1-Cyclohexyl-2-(2-methyl-4-nitrophenylimino)-3-oxa-1-azaspiro[4.4]nonane

HRID 276283Notes

Reaction equation

Cl.Cl[CH2:3][C:4]1([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:8][CH2:7][CH2:6][CH2:5]1.[CH3:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[N:26]=[C:27]=[O:28].CN1CCOCC1>ClCCCl>[CH:10]1([N:9]2[C:4]3([CH2:8][CH2:7][CH2:6][CH2:5]3)[CH2:3][O:28][C:27]2=[N:26][C:18]2[CH:19]=[CH:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][C:17]=2[CH3:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-(chloromethyl)-1-(cyclohexylamino)cyclopentane HCl salt (Method B7b; 1.06 g, 4.2 mmol) and 2-methyl-4-nitrophenyl isocyanate (0.75 g, 4.2 mmol) in 1,2-dichloroethane (10 mL) was added N-methylmorpholine (0.92 mL, 8.4 mmol). The resulting mixture was heated to 50° C. for 18 h, then cooled to 20° C. and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, gradient from hexane to 10% EtOAc/hex) to yield 1-cyclohexyl-2-(2-methyl-4-nitrophenylimino)-3-oxa-1-azaspiro[4.4]nonane (0.021 g, 1.4%): CI-MS m/z 358 ((M+H)+).

Workup

temperaturecooled to 20° C.
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography (SiO2, gradient from hexane to 10% EtOAc/hex)

Sources & evidence

ORD record: ord-50b49bb609724cc98c3ea8dad3bf1c65
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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