Acetonitrile → HCID 117992315, compound

HRID 531031Notes

Reaction equation

HRID 531031 reaction equation
[CH:1]([C:3]1[C:8]([C:9]([O:11]C)=O)=[CH:7][C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][N:4]=1)=[CH2:2].[NH2:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.CCN(C(C)C)C(C)C.C(#N)C>CO>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:18]([N:17]2[CH2:2][CH2:1][C:3]3[N:4]=[CH:5][C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][C:8]=3[C:9]2=[O:11])[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 18458767HCID 18458767, compound

Product 1

HCID 117992315HCID 117992315, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of dimethyl 2-vinylpyridine-3,5-dicarboxylate (1.8 g), tert-butyl 4-aminopiperidine-1-carboxylate (2.4 g), N,N′-diisopropylethylamine (2.13 mL), acetonitrile (10 mL), and methanol (10 mL) was stirred at 150° C. for 16 hours under microwave irradiation. The reaction mixture was allowed to cool to room temperature, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.8 g).

Workup

  1. temperatureto cool to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-60e543140ec04e1d8412c2210757dc70
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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