Acetic Acid → Dimethylaminomethylbenzylcyanide

HRID 893266Notes

Reaction equation

HRID 893266 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4](O)CCC.C(O)(=O)C.O.BrC[C:16]1[CH:24]=[CH:23][C:19]([CH2:20][C:21]#[N:22])=[CH:18][CH:17]=1>CO>[CH3:1][N:2]([CH2:4][CH:20]([C:21]#[N:22])[C:19]1[CH:18]=[CH:17][CH:16]=[CH:24][CH:23]=1)[CH3:3]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 2631-ButanolHCID 674DimethylamineHCID 962WaterHCID 143420762-(4-(Bromomethyl)phenyl)acetonitrile

Product 1

HCID 415903Dimethylaminomethylbenzylcyanide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a 1 liter round bottomed flask with condenser and thermometer 8.2 g of 4-bromomethylbenzylcyanide are dissolved in 453 ml methanol and cooled to +3° C. At this temperature 12.7 ml of 40% dimethylamine solution are added drop-by-drop. The solution is subsequently stirred for 1/4 hour at +5° C. and 2 hours at room temperature. The reaction sequence is controlled by means of thin-layer chromatography (0.57 ml of specimen+0.43 ml methanol: eluent n-butanol: acetic acid: water=4:1:1; v/v; 10 μl coating; HPTLC finished plated diatomaceous earth 60 F 254). Following removal of the volatile components is a rotary evaporator (20 torr, 40° C. bath temperature) the residue is absorbed in 20 ml 1N hydrochloric acid and extracted with a total of 150 ml of diethyl ether. The clear, aqueous phase is treated with 30 ml of 1N sodium hydroxide solution (ice cold) and extracted subsequently with 250 ml of diethyl ether. The organic phase is washed to neutrality with a saturated solution of common salt, dried with sodium sulfate and evaporated to dryness in a rotary evaporator (30° C. bath temperature, 20 torr).

Workup

  1. temperaturecooled to +3° C
  2. customremoval of the volatile components
  3. customa rotary evaporator (20 torr, 40° C. bath temperature) the residue
  4. customis absorbed in 20 ml 1N hydrochloric acid
  5. extractionextracted with a total of 150 ml of diethyl ether
  6. additionThe clear, aqueous phase is treated with 30 ml of 1N sodium hydroxide solution (ice cold)
  7. extractionextracted subsequently with 250 ml of diethyl ether
  8. washThe organic phase is washed to neutrality with a saturated solution of common salt
  9. dry with materialdried with sodium sulfate
  10. customevaporated to dryness in a rotary evaporator (30° C. bath temperature, 20 torr)

Sources & evidence

ORD record
ord-370b8ce48f7f48c3bafaecdb5121d806
Source dataset
uspto-grants-1992_06
Patent number
US05124326

Reaction notes

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