Potassium Carbonate → 1-[4-(6-Mercaptohexylthio)-phenyl]-2-methyl-2-morpholine-4-yl-propane-1-one

HRID 376968Notes

Reaction equation

HRID 376968 reaction equation
[CH2:1]([SH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][SH:7].C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:32])[C:23]([CH3:31])([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH3:24])=[CH:18][CH:17]=1>CC(N(C)C)=O.C(OCC)(=O)C>[SH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][S:8][C:16]1[CH:17]=[CH:18][C:19]([C:22](=[O:32])[C:23]([CH3:24])([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[CH3:31])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 144911,6-HexanedithiolHCID 157024081-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

Product 1

HCID 193606291-[4-(6-Mercaptohexylthio)-phenyl]-2-methyl-2-morpholine-4-yl-propane-1-one

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
85 °C

Procedure

10.0 g (0.066 mol) of 1,6-hexanedithiol are added to a suspension of 3.6 g (0.026 mol) of potassium carbonate in 15 ml of dimethylacetamide. The suspension is heated to 85° C., and a solution of 3.6 g (0.013 mol) of 1-(4-chlorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one in 20 ml of dimethylacetamide is added dropwise over 20 min. After stirring for 18 h, the reaction mixture is cooled, diluted with ethyl acetate (60 ml), and filtered. The filtrate is washed with water (3×50 ml), dried over MgSO4, and concentrated i.v. (85° C./5 mm Hg). The resulting oil is purified by flash chromatography on silica gel (hexane/ethyl acetate 85:15) to a pale yellow oil which crystallizes to a colorless solid upon standing. m.p. 61-64° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.31 (s, 6H), 1.35 (t, SH), 1.4-1.8 (m, 8H), 2.53 (q, 2H), 2.57 (t, 4H), 3.00 (t, 2H), 3.69 (t, 4H), 7.24 (d, 2H), 8.50 (d, 2H).

Workup

  1. temperaturethe reaction mixture is cooled
  2. filtrationfiltered
  3. washThe filtrate is washed with water (3×50 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated i.v
  6. custom(85° C./5 mm Hg)
  7. customThe resulting oil is purified by flash chromatography on silica gel (hexane/ethyl acetate 85:15) to a pale yellow oil which
  8. customcrystallizes to a colorless solid

Sources & evidence

ORD record
ord-ceb9e66f9f3042ef9c89b42bdcc16a9c
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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