Piperidine → HCID 44468242, compound

HRID 38958Notes

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.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CO>[Cl:23][C:22]1[C:16]2[O:15][CH2:14][C@H:13]([CH2:12][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[O:18][C:17]=2[CH:19]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.49 g, 1.1 mmol), piperidine (1 ml, 10.1 mmol) and MeOH (2 ml) was heated under microwave radiation at 120° C. for 25 min. Purification on SCX-3 column (TEA/MeOH) and by flash column chromatography (MeOH/EtOAc) gave the title compound (0.31 g). The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et20 (0.25 g). MS m/z (rel. intensity, 70 eV) 345 (M+, 0.5), 124 (3), 99 (7), 98 (bp), 96 (2), 55 (4) [α]=−60° (MeOH).

Workup

customPurification on SCX-3 column (TEA/MeOH)

Sources & evidence

ORD record: ord-a2342d496f994bcb9b8481fa4c1578d2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Reaction notes

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