Piperidine, 1-(2-chloroethyl)-, hydrochloride → 3-Amino-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrile

HRID 1190902Notes

Reaction equation

HRID 1190902 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH2:10])[CH:9]=1)[C:5]#[N:6].Cl.Cl[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CCN(C(C)C)C(C)C>CC(CC)CO>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH:10][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 81531DiisopropylethylamineHCID 128973293,5-Diaminobenzonitrile

Product 1

HCID 672465403-Amino-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 87232-Methyl-1-butanolSolvent

Procedure

3,5-Diaminobenzonitrile prepared from step A of example 19 (511 mg, 3.84 mmol), 1-(2-chloroethyl)piperidine hydrochloride (707 mg, 1 eq) and DIEA (1.97 mL, 3 eq) were refluxed in 50 mL of 2-methylbutan-1-ol for 24 h. The reaction mixture was then evaporated to give 751 mg of expected compound which was used in the next step without further purification. m/z (ESI) 245.3 [M+H]+.

Workup

  1. customThe reaction mixture was then evaporated

Sources & evidence

ORD record
ord-b43f3a9211fd434b80aab25bc025fdb2
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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