Cyanuric chloride → tert-Butyl 4-cyano-4-isopropylpiperidine-1-carboxylate

HRID 2093600Notes

Reaction equation

HRID 2093600 reaction equation
[NH2:1][C:2]([C:4]1([CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)=O.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C)C=O.O.C(OCC)(=O)C>[C:2]([C:4]1([CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:6][CH2:5]1)#[N:1]

Participants

6

Reactant 2

HCID 7954Cyanuric chlorideHCID 68728193tert-Butyl 4-carbamoyl-4-isopropylpiperidine-1-carboxylate

Product 1

HCID 68787901tert-Butyl 4-cyano-4-isopropylpiperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(aminocarbonyl)-4-isopropylpiperidine-1-carboxylate (100 mg, 0.370 mmol) in dimethylformamide (2 ml) was added cyanuric chloride (34.1 mg, 0.185 mmol). After stirring over the weekend at room temperature, the mixture was diluted with 10 ml of water, and 20 ml of ethyl acetate. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×15 ml). The combined organics were washed with 10 ml each of saturated sodium bicarbonate solution and brine, dried (sodium sulfate), and then concentrated to provide the title compound (93 mg, 0.369 mmol, 100% yield). Mass spectrum (ESI) 153.2.0 (M-Boc).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×15 ml)
  3. washThe combined organics were washed with 10 ml each of saturated sodium bicarbonate solution and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-84c3e8b6d41b4bdeb45e87e505f1cb57
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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