Hydrochloric Acid → N-Methyl-1-[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanamine

HRID 38902Notes

Reaction equation

HRID 38902 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH3:27][NH2:28].Cl>C(#N)C>[CH3:27][NH:28][CH2:12][C@@H: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[O:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 86652935[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 66900146N-Methyl-1-[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 3 using [(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.4 g, 1 mmol), methanamine (33% in EtOH, 1 ml) and ACN (3 ml). Yield: 0.2 g, 89%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 248° C. MS m/z (rel. intensity, 70 eV) 257 (M+, bp), 79 (86), 70 (59), 63 (50), 51 (71). [α]=−59° (MeOH).

Workup

  1. customPreparation
  2. customcrystallized from MeOH/Et2O
  3. custom[α]=−59° (MeOH)

Sources & evidence

ORD record
ord-d84aadf79e9d4b37a7fc8f1cc9cf6258
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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