Hydrogen Peroxide → Dimethyl-(4-{4-[3-(1-oxothiomorpholin-4-yl)propoxy]phenyl}-tetrahydropyran-4-ylmethyl)amine

HRID 272819Notes

Reaction equation

[CH3:1][N:2]([CH3:26])[CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][S:23][CH2:22][CH2:21]3)=[CH:12][CH:11]=2)[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C(O)(C(F)(F)F)=[O:28].FC(F)(F)C(OO)=O.OO.[OH-].[Na+]>C(Cl)Cl>[CH3:26][N:2]([CH3:1])[CH2:3][C:4]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][S:23](=[O:28])[CH2:24][CH2:25]3)=[CH:14][CH:15]=2)[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1

Participants

Conditions

Temperature: 2.5 °C

Procedure

Dimethyl-{4-[4-(3-thiomorpholin-4-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}amine (300 mg, 0.792 mmol) and TFA (0.99 ml) were cooled to 0 to 5° C. and trifluoro-peracetic acid (4M, 0.77 ml) [4M solution prepared by the addition of 27.5% H2O2 (0.94 ml) to TFA (1.56 ml)] was added and the reaction stirred for six hours at 0 to 5° C. The mixture was diluted with DCM (6 ml), basified with NaOH (2M, 8 ml) and extracted with DCM (2×20 ml). The DCM extracts were dried over MgSO4, filtered and concentrated in vacuo at 35° C. Purification by chromatography on silica, eluant DCM:MeOH:NH3 (96:4:1) provided the title compound (200 mg, 61%) as a white solid. 1H NMR (400 MHz, CDCl3) δ7.21 (d, 2H), 6.86 (d, 2H), 4.01 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 3.15-3.02 (m, 2H), 2.93-2.79 (m, 4H), 2.72 (dt, 2H), 2.64 (t, 2H), 2.40 (s, 2H), 2.16-1.82 (m, 6H), 1.97 (s, 6H).

Workup

additionwas added
extractionextracted with DCM (2×20 ml)
dry with materialThe DCM extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo at 35° C
customPurification by chromatography on silica, eluant DCM:MeOH:NH3 (96:4:1)

Sources & evidence

ORD record: ord-8dda7e449c3f48cf81e5db2627bc4408
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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