Trifluoroacetic acid → (4-{4-[3-(1,1-Dioxo-thiomorpholin-4-yl)propoxy]phenyl}tetra-hydro-pyran-4-ylmethyl)dimethyl-amine

HRID 272820Notes

Reaction equation

HRID 272820 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.[OH-:42].[Na+]>C(Cl)Cl>[O:42]=[S:23]1(=[O:28])[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][O:16][C:13]2[CH:12]=[CH:11][C:10]([C:4]3([CH2:3][N:2]([CH3:1])[CH3:26])[CH2:5][CH2:6][O:7][CH2:8][CH2:9]3)=[CH:15][CH:14]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 10290812Trifluoroperacetic acidHCID 59837475Dimethyl-{4-[4-(3-thiomorpholin-4-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}amine

Product 1

HCID 59837527(4-{4-[3-(1,1-Dioxo-thiomorpholin-4-yl)propoxy]phenyl}tetra-hydro-pyran-4-ylmethyl)dimethyl-amineYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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) was added and the reaction allowed to warm to ambient temperature overnight. 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 (151 mg, 46%) as a white solid. 1H NMR (400 MHz, CDCl3) δ7.22 (d, 2H), 6.85 (d, 2H), 4.01 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 3.10-2.97 (m, 8H), 2.72 (t, 2H), 2.40 (s, 2H), 2.14-1.82 (m, 6H), 1.97 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-513936c06b264c8da30344859b0d4f55
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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