1,3,5-Trimethyl-1,3,5-triazacyclohexane → Rac-5-cyclohexyl-1-methyl-5-nitro-piperidin-2-one

HRID 2177487

Reaction equation

HRID 2177487 reaction equation
CO[C:3](=[O:16])[CH2:4][CH2:5][CH:6]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[N+:7]([O-:9])=[O:8].[CH3:17][N:18]1CN(C)CN(C)[CH2:19]1>>[CH:10]1([C:6]2([N+:7]([O-:9])=[O:8])[CH2:17][N:18]([CH3:19])[C:3](=[O:16])[CH2:4][CH2:5]2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 79521,3,5-Trimethyl-1,3,5-triazacyclohexaneHCID 59438496Rac-4-cyclohexyl-4-nitro-butyric acid methyl ester

Product 1

HCID 59438407Rac-5-cyclohexyl-1-methyl-5-nitro-piperidin-2-oneYield 57.4%

Conditions

Temperature
100 °C

Procedure

To 4.25 g (18.5 mmol) rac-4-cyclohexyl-4-nitro-butyric acid methyl ester were added 4.56 ml (32.5 mmol) 1,3,5-trimethylhexahydro-1,3,5-triazine and the mixture heated to 100° C. for 4 hours. The reaction mixture was cooled to ambient temperature and adsorbed on silica gel which was transferred on top of a silica gel column and purified by flash-chromatography with a gradient of heptane and 10 to 75% ethyl acetate: 2.55 g of title compound were isolated as colourless oil: MS (m/e): 240 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. custompurified by flash-chromatography with a gradient of heptane and 10 to 75% ethyl acetate

Sources & evidence

ORD record
ord-bb8e62a8a3df4f6bb21e03134e2b40a3
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Linked notes

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