Propylamine → HCID 44469323, compound

HRID 38893Notes

Reaction equation

HRID 38893 reaction equation
CC1C=CC(S(O[CH2:12][CH: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][CH: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 86652933[7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 44469323HCID 44469323, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of [7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.4 g, 0.90 mmol), propan-1-amine (1 ml) and ACN (3 ml) was heated under microwave radiation at 120° C. for 30 min. Purification on SCX-3 column (TEA/MeOH) and on a small silica plug (DCM/MeOH). Yield: 0.2 g, 90%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 223° C. MS m/z (rel. intensity, 70 eV) 285 (M+, 5), 256 (4), 207 (5), 73 (5), 72 (bp).

Workup

  1. customPurification on SCX-3 column (TEA/MeOH)
  2. customcrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-0901f4f8e22d42d2a86ba1dc6fb6d1f7
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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