Butylamine → 4'-Butylaminomethyl-2-cyanobiphenyl

HRID 2380668Notes

Reaction equation

HRID 2380668 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])=[CH:10][CH:9]=1>O1CCOCC1>[CH2:1]([NH:5][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 153383534'-Butylaminomethyl-2-cyanobiphenyl

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

36 ml (367 mmol) of butylamine are added to a solution of 20.0 g (73.5 mmol) of 4-bromomethyl-2'-cyano-biphenyl (cf. EP 253,310, page 159) in 150 ml dioxane and the mixture is heated under reflux for 3 hours. The reaction mixture is then concentrated by evaporation in vacuo and the residue is partitioned between 300 ml of diethyl ether and 100 ml of water. The ethereal phase is washed twice with water, dried and concentrated by evaporation. The resulting oil is flash-chromatographed on 500 g of silica gel [toluene/methanol(19:1)]. The fractions containing the product are concentrated by evaporation to yield N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amine in the form of a yellow oil that has an Rf value of 0.34 [toluene/methanol (4:1)].

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture is then concentrated by evaporation in vacuo
  4. customthe residue is partitioned between 300 ml of diethyl ether and 100 ml of water
  5. washThe ethereal phase is washed twice with water
  6. customdried
  7. concentrationconcentrated by evaporation
  8. customThe resulting oil is flash-chromatographed on 500 g of silica gel [toluene/methanol(19:1)]
  9. additionThe fractions containing the product
  10. concentrationare concentrated by evaporation

Sources & evidence

ORD record
ord-4fe0c10d70964eab8b0ae8d300b79c43
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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