Betahistine → 3-[[2-(2-Pyridyl)ethyl]amino]propanenitrile

HRID 1727429

Reaction equation

HRID 1727429 reaction equation
[C:1](#[N:4])[CH:2]=C.[CH3:5][NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1>CO>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][NH:6][CH2:5][CH2:2][C:1]#[N:4]

Participants

4

Reactant 2

HCID 2366BetahistineHCID 7855Acrylonitrile

Product 1

HCID 27773663-[[2-(2-Pyridyl)ethyl]amino]propanenitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Acrylonitrile (10.1 ml, 1.1 eq) is added slowly to a solution cooled down to approximately 4° C. of 2-[2-(methylamino)ethyl]pyridine (19.5 ml, 1 eq) in methanol (200 ml). The reaction medium is then stirred for 3 hours at approximately 20° C. then concentrated under reduced pressure at 40° C. in order to produce 3-[(2-pyridin-2-ylethyl)amino]propanenitrile in the form of a yellow oil (25.6 g, 96% yield).

Workup

  1. concentrationthen concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record
ord-0266a41d973147b9b96ce8557e7e5fe5
Source dataset
uspto-grants-2009_02
Patent number
US07495110B2

Linked notes

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