Piperazine → 4-(2-Cyano-5-methyl-phenyl)-piperazine

HRID 1592746Notes

Reaction equation

Br[C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:2]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)#[N:5]

Participants

Reactant 2

HCID 4837Piperazine

HCID 8208022-Bromo-4-methylbenzonitrile

Product 1

HCID 179523334-(2-Cyano-5-methyl-phenyl)-piperazine

Procedure

2-Bromo-4-methyl-benzonitrile was coupled to piperazine using Preparation 1A Buchwald chemistry to afford 4-(2-cyano-5-methyl-phenyl)-piperazine. 4-(2-cyano-5-methyl-phenyl)-piperazine is converted to 4(2-hydroxymethyl-5-methyl-phenyl)-piperazine in a manner similar to preparation 54A Steps 1 and 2.4-(2-Hydroxymethyl-5-methyl-phenyl)-piperazine was converted to the title compound in a manner similar to Preparation 60A except that pyrrolidine was used to displace the mesylate. LRMS (ESI+): 360.3 (M+1)

Sources & evidence

ORD record: ord-95f626b4e03646cfb6186228cfe56a24
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291619B2

Reaction notes

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