Propylamine → N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine

HRID 2380675Notes

Reaction equation

HRID 2380675 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1.[CH2:17]([NH2:20])[CH2:18][CH3:19]>C(Cl)Cl>[C:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:20][CH2:17][CH2:18][CH3:19])=[CH:4][CH:5]=1)#[N:16]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 15338355N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.84 g of 4-bromomethyl-2'-cyano-biphenyl are mixed at room temperature with 20 ml of propylamine. The mixture is stirred for 30 minutes, during which heating to reflux temperature occurs, is then diluted with 400 ml of CH2Cl2 and washed with 200 ml of NaHCO3 solution. The organic phase is dried over Na2SO4 and freed of the solvents in vacuo to leave a yellow oil. Purification of the latter by chromatography on silica gel 60 (40-63 μm) using CH2Cl2 /CH3OH (98:2) as eluant yields pure N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine that has an Rf value of 0.15 [CH2Cl2 /CH3OH (95:5)].

Workup

  1. temperatureheating
  2. temperatureto reflux temperature
  3. washwashed with 200 ml of NaHCO3 solution
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customto leave a yellow oil
  6. customPurification of the latter by chromatography on silica gel 60 (40-63 μm)

Sources & evidence

ORD record
ord-e52320bc690140099df54eccb7b8fa36
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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