Butylamine → 4'-Butylaminomethyl-2-cyanobiphenyl

HRID 1440797Notes

Reaction equation

HRID 1440797 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]([NH2:21])[CH2:18][CH2:19][CH3:20]>O1CCCC1>[CH2:17]([NH:21][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)[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

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

Product 1

HCID 153383534'-Butylaminomethyl-2-cyanobiphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4'-bromomethyl-2-cyanobiphenyl (10.0 g) in tetrahydrofuran (100 ml) was added butylamine (26.8 g). The mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated and diluted with water, followed by extraction with chloroform. The extract was washed with water and dried. The solvent was distilled under reduced pressure. The residue was purified by column chromatography on silica gel to afford the title compound as a pale yellow oil (10.7 g, quantitatively).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. distillationThe solvent was distilled under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-16b7843beb724b3ea2bfad8d01a32248
Source dataset
uspto-grants-1996_03
Patent number
US05500427

Reaction notes

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