Dimethylamine → 3-(dimethylaminomethyl)benzonitrile

HRID 1804548Notes

Reaction equation

HRID 1804548 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[CH3:11][NH:12][CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[CH3:11][N:12]([CH2:6][C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2])[CH3:13]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 90670m-FormylbenzonitrileHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 46410883-(dimethylaminomethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

5.00 g (37.37 mmol) 3-cyanobenzaldehyde and 20.00 ml (40 mmol) dimethylamine (2 molar solution in tetrahydrofuran) are placed in 150 ml of tetrahydrofuran and cooled to 0° C. 12.40 g (81.73 mmol) sodium triacetoxyborohydride are added, then the mixture is stirred for 2 hours at 0° C. and 2 hours at ambient temperature. The reaction mixture is combined with 25 ml of 15% potassium carbonate solution and stirred for 0.5 hours. After the addition of ethyl acetate the mixture is extracted. The organic phase is washed with potassium carbonate solution, dried and evaporated to dryness.

Workup

  1. stirringstirred for 0.5 hours
  2. extractionis extracted
  3. washThe organic phase is washed with potassium carbonate solution
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-357828be552e4ee19b4fff3cd2c8e243
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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