Piperazine → Piperidine

HRID 600461Notes

Reaction equation

HRID 600461 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>>[C:8]([CH2:9][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)#[N:7].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 8082Piperidine

Product 2

HCID 8082PiperidineHCID 15522031(Piperazin-1-yl)acetonitrile

Procedure

The secondary amine of a functionalized piperazine or piperidine can be alkylated with a haloacetonitrile under basic conditions to yield a cyanomethyl piperazine or piperidine analogue. In a typical procedure N-benzoyl piperazine was added to a solution of chloroacetonitrile and TEA in THF and stirred at r.t. for between 2 and 5 days. A resulting precipitate is removed by filtration, the filtrate is concentrated in vacuo, and the residue purified via chromatography to yield the cyanomethyl intermediate YCH2CN. The alkylation with haloacetonitrile can also be carried out with an alternate base, such as 4-methylmorpholine or diisopropylethyl amine.

Sources & evidence

ORD record
ord-77746547bd584fc1a2a108075fd1cd12
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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