N,N,N',N'-Tetramethylethylenediamine → Tert-butyl 1'-(6-cyanopyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

HRID 2093457Notes

Reaction equation

CS(C1C=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=CC=1)(=O)=O.C[N:31](C)[CH2:32][CH2:33][N:34](C)C.C1(P(C2C=CC=CC=2)CCCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C-:69]#[N:70].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:69]([C:32]1[N:31]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:21][CH2:22]3)[CH2:13][CH2:12]2)[CH:9]=[N:34][CH:33]=1)#[N:70]

Participants

Conditions

Temperature: 160 °C

Procedure

The tert-butyl 1′-[4-(methylsulfonyl)phenyl]-4,4′-bipiperidine-1-carboxylate (500 mg, 1.3 mmol), palladium(II) acetate (6 mg, 0.026 mmol),N,N,N′,N′-tetramethylethylenediamine (0.15 mL, 0.26 mmol), 1,5-bis(dipenylphosphino)pentane, potassium cyanide (93 mg, 1.43 mmol) were add in a seal bottle with 13 mL anhydrous toluene. The mixture was degassed by N2 and closed and heated to 160° C. overnight (16 h). The reaction was cooled down to r.t. and diluted with ethyl acetate 50 mL, filtered through celite, and concentrated on rotavapor. The crude material was purified by silica gel flash chromatography with 30% acetone: hexane to yield the title compound.

Workup

customThe mixture was degassed by N2
customclosed
temperatureThe reaction was cooled down to r.t.
additiondiluted with ethyl acetate 50 mL
filtrationfiltered through celite
concentrationconcentrated on rotavapor
customThe crude material was purified by silica gel flash chromatography with 30% acetone

Sources & evidence

ORD record: ord-91b608bb866d42e5a0137d901737a305
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445499B2

Reaction notes

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