Hydrochloric Acid → 1-{[(2S)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}piperidine

HRID 38899Notes

Reaction equation

HRID 38899 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.Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 86652935[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 444695951-{[(2S)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}piperidine

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), piperidine (1 ml) and ACN (3 ml). Yield: 0.3 g, 94%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 227° C. MS m/z (rel. intensity, 70 eV) 311 (M+, 1), 310 (M+, 1), 99 (7), 98 (bp), 79 (2), 55 (4). [α]=−65° (MeOH).

Workup

  1. customPreparation
  2. customcrystallized from MeOH/Et2O
  3. custom[α]=−65° (MeOH)

Sources & evidence

ORD record
ord-16b71b8e120d4bb6982c7b1a6a606d22
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

Loading…