Ethanol → 2-Methyl-5-phenylbenzylamine

HRID 1883638Notes

Reaction equation

HRID 1883638 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].C(O)C.O.N>O1CCOCC1.[Ni].O>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

7

Reactant 3

HCID 702Ethanol2×HCID 111715372-Methyl-5-phenylbenzonitrileHCID 12896473Azane;hydrate2×

Product 1

HCID 235082132-Methyl-5-phenylbenzylamineYield 93.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalyst2×HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

4.46 g (23.1 mmol) of 2-methyl-5-phenylbenzonitrile was dissolved in 26 ml of 1,4-dioxane and to this was added 5 ml of ethanol. To this solution was added 9 ml of 28 wt % ammonia water, and 3 g of a suspension of Raney nickel W2 (manufactured by Aldrich; 50 wt % in water). This mixture was stirred for 8 hours at room temperature under hydrogen atmosphere. To this mixture was further added 2 g of a suspension of Raney nickel W2 (manufactured by Aldrich; 50 wt % in water), 8 ml of 28 wt % ammonia water and 20 ml of ethanol, and the mixture was stirred for 4.5 hours at room temperature under hydrogen atmosphere. The reaction mixed was filtrated through celite, and the filtrate was concentrated. The residue was distilled by using Kugelrohl distillation apparatus (0.5 mmHg, set temperature: 216° C.), to obtain 4.25 g of 2-methyl-5-phenylbenzylamine.

Workup

  1. stirringthe mixture was stirred for 4.5 hours at room temperature under hydrogen atmosphere
  2. additionThe reaction mixed
  3. filtrationwas filtrated through celite
  4. concentrationthe filtrate was concentrated
  5. distillationThe residue was distilled
  6. distillationKugelrohl distillation apparatus (0.5 mmHg, set temperature: 216° C.)

Sources & evidence

ORD record
ord-516c299f5876434a91b32d53289176b2
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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