Dimethylamine → 3-(dimethylaminomethyl)benzonitrile

HRID 1386954Notes

Reaction equation

HRID 1386954 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH3:11][NH:12][CH3:13].CCOCC>O>[CH3:11][N:12]([CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])[CH3:13]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 3283Diethyl EtherHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 46410883-(dimethylaminomethyl)benzonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-(bromomethyl)-benzonitrile (3 g, 15.3 mmol) and a solution of 40% dimethylamine in water was heated in a sealed teflon vessel under microwave irradiation (7 min, 600 watts, 150° C., 11 bar). After cooling the resulting mixture was partioned between water and ether, the aqueous phase was extracted three times with ether, washed with satd. NaCl then dried with Na2SO4 and the solvent evaporated. The resulting yellow oil was distilled in a Kugelrohr apparatus at 60-80° C. and 0.002 mbar affording the title compound (1.53 g, 9.55 mmol, 62% yield) as a pale yellow oil. MS: m/e=160 (M+).

Workup

  1. temperatureAfter cooling the resulting mixture
  2. extractionthe aqueous phase was extracted three times with ether
  3. washwashed with satd
  4. dry with materialNaCl then dried with Na2SO4
  5. customthe solvent evaporated
  6. distillationThe resulting yellow oil was distilled in a Kugelrohr apparatus at 60-80° C.

Sources & evidence

ORD record
ord-8e5b642839004572990ac9949e55bf6a
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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