Sodium Hydroxide → HCID 59850551, compound

HRID 1012569Notes

Reaction equation

HRID 1012569 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH3:10])[CH2:2][CH3:3].[OH-].[Na+].[H][H]>[Ni].C(O)C>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][NH2:17])=[CH:18][CH:19]=1)[CH3:10])[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 161172934-[(4-Dipropylaminobutyl)methylamino]methylbenzonitrileHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59850551HCID 59850551, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

14.6 g of 4-[(4-dipropylaminobutyl)methylamino]methylbenzonitrile (2b), 292 ml of ethanol, and 102 ml of a 1N sodium hydroxide aqueous solution were charged in a 1-liter recovery flask. 1.46 g (10 wt %) of Raney nickel prepared using the method described in Example 1 was slowly added to the solution. After replacing the atmosphere in the flask with nitrogen and then with hydrogen, the mixture was stirred at room temperature for 17 hours using a hydrogen balloon. After confirming the disappearance of the raw material, the catalyst was removed by celite filtration, and the product was washed with 70% ethanol solution. The obtained filtrate was concentrated under reduced pressure. After the addition of 100 ml of distilled water to the residue, the product was extracted twice with 200 ml of hexane. The organic layer was washed with 100 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 14.5 g of 4-[(4-dipropylaminobutyl)methylamino]methylbenzylamine (13) as a yellow oily substance (yield: 98%, GC: 93%). [HPLC: 90% (HPLC measurement conditions A)]

Workup

  1. additionwas slowly added to the solution
  2. customthe catalyst was removed by celite filtration
  3. washthe product was washed with 70% ethanol solution
  4. concentrationThe obtained filtrate was concentrated under reduced pressure
  5. additionAfter the addition of 100 ml of distilled water to the residue
  6. extractionthe product was extracted twice with 200 ml of hexane
  7. washThe organic layer was washed with 100 ml of a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-388e2389d7444545840ea57fdd5aa6ba
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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