3-Phenylpropylamine → 2-Bromo-4-((3-phenylpropyl)amino)nicotinonitrile

HRID 1615906Notes

Reaction equation

HRID 1615906 reaction equation
[Br:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6](Br)[C:3]=1[C:4]#[N:5].[NH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 574595912,4-Dibromopyridine-3-carbonitrile

Product 1

HCID 866965062-Bromo-4-((3-phenylpropyl)amino)nicotinonitrileYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the methods above using 2,4-dibromonicotinonitrile (100 mg, 0.382 mmol), 3-aminopropylbenzene (0.058 mL, 0.401 mmol) and Hunig's Base (0.080 mL, 0.458 mmol) in DMF (1.5 mL) to give the desired product as a white solid (79 mg). LC/MS (316/318, [M−H]−/[M+H]+); 1H NMR (400 MHz, CHLOROFORM-d) δ 8.02 (dd, J=6.0, 0.5 Hz, 1H), 7.37-7.30 (m, 2H), 7.28-7.15 (m, 3H), 6.42 (d, J=6.0 Hz, 1H), 5.26 (br. s., 1H), 3.28 (td, J=7.0, 5.8 Hz, 2H), 2.75 (t, J=7.4 Hz, 2H), 2.03 (quin, J=7.3 Hz, 2H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-269714bc15ea437eabc1f30ca6fa4487
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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