Propylamine → HCID 44469450, compound

HRID 38894Notes

Reaction equation

HRID 38894 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.[CH2:27]([NH2:30])[CH2:28][CH3:29]>C(#N)C>[CH3:26][S:23]([C:20]1[CH:21]=[CH:22][C:16]2[O:15][CH2:14][C@@H:13]([CH2:12][NH:30][CH2:27][CH2:28][CH3:29])[O:18][C:17]=2[CH:19]=1)(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 86652934[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 44469450HCID 44469450, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of [(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.7 g, 1.8 mmol), propan-1-amine (1 ml) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and flash column chromatography (EtOAc/MeOH). Yield: 0.4 g, 73%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 228° C. MS m/z (rel. intensity, 70 eV) 285 (M+, 3), 207 (4), 73 (5), 72 (bp), 70 (5). [α]=+67° (MeOH).

Workup

  1. customPurification on SCX-3 column (TEA/MeOH) and flash column chromatography (EtOAc/MeOH)
  2. customcrystallized from MeOH/Et2O
  3. custom[α]=+67° (MeOH)

Sources & evidence

ORD record
ord-0c367b480992494aa92191ac61b3673b
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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