HCID 15965417, compound → HCID 59850548, compound

HRID 1012571Notes

Reaction equation

HRID 1012571 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH2:2][CH3:3].C[O-].[Na+].CO.[H][H]>[Ni].CO>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:17][CH:18]=1)[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 15965417HCID 15965417, compoundHCID 23694274Sodium methanolate methanolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59850548HCID 59850548, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4.0 g (13.91 mmol, 1.0 equivalent) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a) and 24 ml of methanol were charged in a 100 ml three-necked flask. 400 mg (10 wt %) of the Raney nickel prepared in Example 1 was then slowly added to the mixture. After the addition of 2.58 g (13.35 mmol, 0.96 equivalents) of a 28% sodium methoxide/methanol solution, the atmosphere in the flask was replaced with nitrogen and then with hydrogen. The mixture was then stirred at room temperature for five days using a hydrogen balloon. After completion of the reaction, the reaction solution was filtered through celite. After concentration, the resulting residue was added to 50 ml of water. The product was extracted with 100 ml of chloroform three times. The chloroform layer was washed twice with 100 ml of water, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 4.0 g of 4-[(4-dipropylaminobutyl)amino]methylbenzylamine (5a) as a colorless oily substance (yield: 99%, GC: 96.0%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered through celite
  3. concentrationAfter concentration
  4. additionthe resulting residue was added to 50 ml of water
  5. extractionThe product was extracted with 100 ml of chloroform three times
  6. washThe chloroform layer was washed twice with 100 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d5cd777e5c66407780f40c0b88f359e9
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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