(+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}ethanamine → N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}ethanamine

HRID 452402Notes

Reaction equation

HRID 452402 reaction equation
[CH2:1]([N:8]([CH2:11][CH:12]1[O:17][C:16]2[CH:18]=[C:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:20]=[CH:21][C:15]=2[CH2:14][O:13]1)CC)[C:2]1C=CC=CC=1>[Pd].CCO>[CH3:25][S:22]([C:19]1[CH:20]=[CH:21][C:15]2[CH2:14][O:13][CH:12]([CH2:11][NH:8][CH2:1][CH3:2])[O:17][C:16]=2[CH:18]=1)(=[O:23])=[O:24]

Participants

4

Reactant 1

HCID 67155941(+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}ethanamine

Product 1

HCID 44481361N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}ethanamineYield 73.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation according to Example 10. (+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}ethanamine (0.42 g, 1.16 mmol), palladium on carbon (10%, 30 mg) and EtOH (10 ml) was hydrogenated at 50 psi for 7 h. Purification afforded the pure title compound (0.23 g, 73%, >95% e.e). The amine was converted into the hydrochloric acid salt and crystallized from EtOH/MeOH/DEE. M.p. 218° C. [α]DMeOH=+77°. 1H-NMR (400 MHz, CDCl3): δ 7.51 (1H, dd, J1 7.6 Hz, J2 1.6 Hz), δ 7.47 (1H, d, J 1.6 Hz), δ 7.19 (1H, d, J 7.6 Hz), δ 5.21 (1H, t, J 5.2 Hz), δ 5.01 (2H, dd, J1 49 Hz, J2 15 Hz), δ 3.05 (3H, s), δ 2.78 (2H, m), δ 1.45 (1H, s), δ 1.80 (3H, t, J 7.2 Hz).

Workup

  1. customPreparation
  2. customPurification

Sources & evidence

ORD record
ord-002f8872f3f545ef8510d66aa450233f
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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