Sodium Iodide → Benzyl 2-cyclohexyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 215943Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]1([C:20]([O:22]C)=O)[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1.[CH:24]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH:24]1([N:30]2[CH2:2][CH2:3][C:4]3([CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)=[O:11])[CH2:8][CH2:9]3)[C:20]2=[O:22])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate (0.5 g, 0.001 mol), cyclohexanamine (0.18 mL, 0.0016 mol), sodium iodide (0.22 g, 0.0015 mol) and potassium carbonate (0.61 g, 0.0044 mol) in DMF (5.0 mL) was stirred and heated at 120° C. for overnight. Then the reaction mixture was diluted with brine, and extracted with ethyl acetate (3X). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by combiflash (ethyl acetate in hexanes: 40%) to give 180 mg of benzyl 2-cyclohexyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate.

Workup

extractionextracted with ethyl acetate (3X)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by combiflash (ethyl acetate in hexanes: 40%)

Sources & evidence

ORD record: ord-f6ad03e7e65e49de8e2381d668032cee
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193207B2

Reaction notes

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