(+)-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 452401Notes

Reaction equation

HRID 452401 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 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(−)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}ethanamine (0.47 g, 1.30 mmol), palladium on carbon (10%, 30 mg) and EtOH (15 ml) was hydrogenated at 50 psi for 13 h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated to dryness (0.34 g). Purification by flash chromatography (EtOAc/MeOH 4:1) afforded the pure title compound (0.27 g, 77%, >95% e.e.). The amine was converted into the hydrochloric acid salt and crystallized from EtOH/MeOH/DEE. M.p 219° C. [α]DMeoH=−79°. 1H-NMR (400 MHz, CDCl3): δ 7.49 (1H, dd, J1 8.0 Hz, J 2 2.0 Hz), δ 7.45 (1H, d, J 2.0 Hz), δ 7.17 (1H, d, J 8.0 Hz), δ 5.19 (1H, t, 4.8 Hz), δ 5.0 (2H, dd, J1 49 Hz, J2 15 Hz), δ 3.03 (3H, s), δ 2.76 (2H, q, J 7.2 Hz), δ 1.46 (1H, s), δ 1.16 (3H, t, J 7.2 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customthe filtrate was evaporated to dryness (0.34 g)
  3. customPurification by flash chromatography (EtOAc/MeOH 4:1)

Sources & evidence

ORD record
ord-194a0b5c389d4465aac0c61266989ce4
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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