Hydrochloric Acid → N-{[(2S)-5-Chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}ethanamine

HRID 38923Notes

Reaction equation

HRID 38923 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[C:22]([Cl:23])[C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH2:28]([NH2:30])[CH3:29].Cl>C(#N)C>[Cl:23][C:22]1[C:16]2[O:15][CH2:14][C@H:13]([CH2:12][NH:30][CH2:28][CH3:29])[O:18][C:17]=2[CH:19]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 86652939[(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 44470011N-{[(2S)-5-Chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}ethanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 5 using [(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.47 g, 1.09 mmol), ethanamine (1 ml, 70% in water) and ACN (7 ml). Yield: 0.278 g, 83%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 267° C. MS m/z (rel. intensity, 70 eV) 305 (M+, 4), 63 (3), 59 (4), 58 (bp), 56 (5). [α]=−62° (MeOH).

Workup

  1. customPreparation
  2. customcrystallized from MeOH/Et2O
  3. custom[α]=−62° (MeOH)

Sources & evidence

ORD record
ord-d7c1de8f78f04b72ad9a62200bd3f331
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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