Triethylamine → 4-[N-(3-Benzyloxypropyl)aminomethyl]-2'-cyanobiphenyl

HRID 1739078Notes

Reaction equation

HRID 1739078 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]([O:24][CH2:25][CH2:26][CH2:27][NH2:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>O1CCOCC1>[CH2:17]([O:24][CH2:25][CH2:26][CH2:27][NH:28][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)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 71307843-(benzyloxy)propan-1-amine

Product 1

HCID 218404054-[N-(3-Benzyloxypropyl)aminomethyl]-2'-cyanobiphenyl

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6.0 g (22 mmol) of 4-bromomethyl-2'-cyanobiphenyl, 5.8 g (35 mmol) of 3-benzyloxypropylamine (Synthesis 1975, 590) and 3.6 g of triethylamine in 50 ml of 1,4-dioxane is heated to boiling under reflux for 18 hours. After working up analogously to Example 23 a), an oil is obtained which, after flash-chromatographic purification (ethanol:ethyl acetate: 1:4), gives the title compound (TLC system B7; Rf value 0.39).

Workup

  1. temperatureunder reflux for 18 hours
  2. customis obtained which
  3. customafter flash-chromatographic purification (ethanol:ethyl acetate: 1:4)

Sources & evidence

ORD record
ord-58863080f7f94a5aac2b051e30045602
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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