Dimethylformamide → 4-(2-{4-[2-(4-Nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519558Notes

Reaction equation

HRID 1519558 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH3:27][N:28](C=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>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][N:13]2[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([C:27]#[N:28])=[CH:3][CH:4]=3)[CH2:11][CH2:12]2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 675134121-[2-(4-Bromophenyl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazine

Product 1

HCID 680714504-(2-{4-[2-(4-Nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of 1-[2-(4-bromophenyl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazine (100 mg, 0.24 mmol), Zinc cyanide (84 mg, 0.72 mmol), and tetrakis(triphenylphosphine)palladium in DMF (1 mL) was heated to 85° C. for 1 hour. LC showed formation of the desired product, which was separated by mass-directed HPLC. LC-MS (IE, m/z): 365 (M+1)+. (0.079 μM)

Sources & evidence

ORD record
ord-92dd5019d15e42659483e794d8e2cc5a
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…