Acetic Acid → N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-1-amine

HRID 452396Notes

Reaction equation

HRID 452396 reaction equation
[CH2:1]([N:8]([CH2:12][CH:13]1[O:18][C:17]2[CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=[CH:22][C:16]=2[CH2:15][O:14]1)CCC)[C:2]1C=CC=C[CH:3]=1.CC(O)=O>[Pd].CCO>[CH3:26][S:23]([C:20]1[CH:21]=[CH:22][C:16]2[CH2:15][O:14][CH:13]([CH2:12][NH:8][CH2:1][CH2:2][CH3:3])[O:18][C:17]=2[CH:19]=1)(=[O:24])=[O:25]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67155851(+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}propan-1-amine

Product 1

HCID 44481357N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-1-amineYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation according to Example 4. (+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}propan-1-amine (0.21 g, 0.56 mmol), palladium on carbon (10%, 25 mg), concentrated AcOH (0.1 ml) and EtOH (10 ml) was hydrogenated at 40 psi for 1 h 15 min. Purification afforded the title compound (0.14 g, 83%, >95% e.e.) The amine was converted into the hydrochloric acid salt and crystallized from EtOH/MeOH/DEE. M.p. 235° C. [α]DMeOH=+77°. 1H-NMR (400 MHz, MeOH): δ 7.50 (1H, dd, J1 8.4 Hz J2 2.0 Hz), δ 7.41 (1H, d, J 1.6 Hz), δ 7.31 (1H, d, J 7.6 Hz), δ 5.25 (1H, t, J 5.2 Hz), δ 5.03 (2H, dd, J1 50 Hz, J2 16 Hz), δ 3.10 (3H, s), δ 2.97 (2H, m), δ 2.65 (2H, t, J 7.2 Hz), δ 1.56 (2H, m), δ 0.95 (3H, t, J 7.6 Hz).

Workup

  1. customPreparation
  2. customPurification

Sources & evidence

ORD record
ord-60cebf3c22854745a19b178c53722e2f
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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