Dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amine → HCID 57461076, compound

HRID 1361725Notes

Reaction equation

HRID 1361725 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]2[O:20][CH2:19][CH2:18][O:17]2)=[CH:11][C:10]=1[CH3:21])C1C=CC=CC=1>C(O)C.O>[O:17]1[CH2:18][CH2:19][O:20][CH:16]1[C:12]1[C:13]([CH3:15])=[CH:14][C:9]([NH2:8])=[C:10]([CH3:21])[CH:11]=1

Participants

4

Reactant 1

HCID 57461075Dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amine

Product 1

HCID 57461076HCID 57461076, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The crude dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amine was dissolved in a 2:1 mixture of ethanol and water (150 mL total) and the resulting mixture was purged with dry nitrogen for 5 minutes. Palladium on carbon (2.3 g, 10 wt. % containing about 50% water) and solid sodium bicarbonate (1.0 g) were added and the resulting mixture was hydrogenated at about 1 atm of hydrogen at 25° C. to 30° C. for about 8 hours. The mixture was then filtered through Celite and the filtrate was concentrated on a rotary evaporator to provide crude 4-[1,3]dioxolan-2-yl-2,5-dimethylphenylamine (5.6 g, 92% yield) as a thick oil. 1H NMR (300 MHz, DMSO-d6) δ 2.05 (s, 3H), 2.22 (s, 3H), 3.7-3.9 (m, 4H), 3.95 (s, 4H), 5.59 (s, 1H), 6.72 (s, 1H), 7.0-7.25 (m, 11H).

Workup

  1. customthe resulting mixture was purged with dry nitrogen for 5 minutes
  2. additionPalladium on carbon (2.3 g, 10 wt. % containing about 50% water) and solid sodium bicarbonate (1.0 g) were added
  3. filtrationThe mixture was then filtered through Celite
  4. concentrationthe filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-38b07d7f8d5745f280741a0a40f2d6c0
Source dataset
uspto-grants-2011_02
Patent number
US07880010B2

Reaction notes

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