Acetic Acid → 3-(dimethylaminomethyl)benzonitrile

HRID 1737279Notes

Reaction equation

HRID 1737279 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].CC(O)=O.[CH3:15][NH:16][CH3:17].[BH3-]C#N.[Na+]>CO>[CH3:15][N:16]([CH2:6][C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 90670m-FormylbenzonitrileHCID 5003444Sodium cyanoborohydride

Product 1

HCID 46410883-(dimethylaminomethyl)benzonitrileYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-cyanobenzaldehyde (2.50 g, 19 mmol) in MeOH:AcOH (25 ml, 99:1) was added dimethyl amine (2.5 ml, 50 mmol) at 0° C., followed by NaBH3CN (1.80 g, 29 mmol). The mixture was stirred at 0° C. for 18 hours, then evaporated, taken up in EtOAc, washed with 5 KHCO3, brine filtered (Whatman® 1 PS phase separator) and evaporated. The residue was purified by flash chromatography on silica gel (eluant EtOAc:MeOH 98:2 v/v) to give the title compound (1.15 g, 38%).

Workup

  1. customevaporated
  2. washwashed with 5 KHCO3, brine
  3. filtrationfiltered (Whatman® 1 PS phase separator)
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel (eluant EtOAc:MeOH 98:2 v/v)

Sources & evidence

ORD record
ord-d8198d74899e4588933220cd87bd5a72
Source dataset
uspto-grants-1999_10
Patent number
US05962451

Reaction notes

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