1,8-Diazabicyclo(5.4.0)undec-7-ene → Tert-butyl 1'-(5-chloropyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

HRID 2093463Notes

Reaction equation

[N:1]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[Cl:20][C:21]1[CH:26]=[N:25][C:24](Cl)=[CH:23][N:22]=1.N12CCCN=C1CCCCC2>CN1C(=O)CCC1.C(OCC)(=O)C>[C:16]([O:15][C:13]([N:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][N:10]([C:24]3[CH:23]=[N:22][C:21]([Cl:20])=[CH:26][N:25]=3)[CH2:9][CH2:8]2)[CH2:3][CH2:2]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 110 °C

Procedure

The tert-butyl 4,4′-bipiperidine-1-carboxylate (1.27 g, 4.7 mmol) and 2,5-dichloropyrazine (670 mg, 4.5 mmol) were dissolved in NMP (5 ml) at room temperature, and 1,8-diazabicyclo[5.4.0]-undec-7-ene (1 mL, 6.8 mmol) added drop-wise. The mixture was heated at 110° C. for 1 h, allowed to cool to r.t. and diluted with 50 mL of ethyl acetate. The solution was washed with water (10 mL ×1), brine (10 mL ×1), dried over magnesium sulfate, filtered, and concentrated in vac. The residue was purified by chromatography on silica gel with 10% acetone:hexanes to yield the title compound.

Workup

temperatureto cool to r.t.
washThe solution was washed with water (10 mL ×1), brine (10 mL ×1)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vac
customThe residue was purified by chromatography on silica gel with 10% acetone

Sources & evidence

ORD record: ord-ab5a6ca13225499da9cda207106137d6
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445499B2

Reaction notes

Loading…