Piperidine → HCID 44469597, compound

HRID 38900Notes

Reaction equation

HRID 38900 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.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>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][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[O:18][C:17]=2[CH:19]=1)(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86652934[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 44469597HCID 44469597, 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 (0.5 g, 1.1 mmol), piperidine (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 by flash chromatography, first with (DCM/MeOH) as eluent and then (EtOAc/MeOH) as eluent. Yield: 0.2 g, 72%. The amine was converted to the hydrochloric acid salt and crystallized from EtOH/Et2O. M.p. 226° C. MS m/z (rel. intensity, 70 eV) 311 (M+, 1), 310 (M+, 1), 99 (7), 98 (bp), 79 (2), 55 (4). [α]=+62° (MeOH).

Workup

  1. customPurification on SCX-3 column (TEA/MeOH)
  2. customcrystallized from EtOH/Et2O
  3. custom[α]=+62° (MeOH)

Sources & evidence

ORD record
ord-149ad4a3f59f4ea0ac0fc97bb6fe57a7
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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