Piperidine → HCID 66601690, compound

HRID 604313Notes

Reaction equation

HRID 604313 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19](Cl)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[OH-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 66601690HCID 66601690, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

Place 3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (0.4 g, 1.34 mmol, 1 eq) and piperidine (662 μL, 6.69 mmol, 5 eq) in a microwave vial, seal and heat in a CEM™ microwave to 180° C. with up to 300 Watt power for 1 hr. (Caution—pressure build up). Add 2 M aqueous sodium hydroxide solution (5 mL) and DCM (5 mL), and then pass through a hydrophobic frit to separate. Extract the aqueous layer twice with DCM (5 mL) combine the organic extracts and concentrate to give 3′-piperidin-1-yl-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (0.46 g, 99%). MS (m/z): 348.3 (M+1).

Workup

  1. customto separate
  2. extractionExtract the aqueous layer twice with DCM (5 mL)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-248b6991cd3b43a8a22fac5aeffd6a44
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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