Dimethylformamide → tert-Butyl 4-(3-Cyanophenyl)piperazine-1-carboxylate

HRID 606518Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:21][N:22](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:21]([C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1)#[N:22]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1,1-dimethylethyl 4-(3-bromophenyl)piperazine-1-carboxylate obtained in Reference Example 112 (3.10 g, 9.09 mmol), zinc cyanide (0.587 g, 5.00 mmol) and tetrakis(triphenylphosphine)palladium (0.525 g, 0.454 mmol) in DMF (30 mL) was stirred at 80° C. for 12 hr under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (25%-40% ethyl acetate/hexane), and crystallized from hexane to give the title compound as a white powder (2.10 g, 80%).

Workup

washwashed with water and saturated brine
dry with materialdried over sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (25%-40% ethyl acetate/hexane)
customcrystallized from hexane

Sources & evidence

ORD record: ord-bf963ca3b6864f38b9a6343d2bb72ee5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915267B2

Reaction notes

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