Tetrahydrothiopyran-4-one → HCID 10107310, compound

HRID 1743836Notes

Reaction equation

HRID 1743836 reaction equation
[CH3:1][N:2]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5](N)[CH2:4][CH2:3]1.[S:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CC.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:9][CH2:8][C:7]2=[C:6]3[C:13](=[CH:12][CH:11]=[CH:10]2)[C:17]2[CH2:16][S:15][CH2:20][CH2:19][C:18]=2[N:5]3[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 66173Tetrahydrothiopyran-4-oneHCID 521998p-Toluenesulfonic acid monohydrateHCID 22236594HCID 22236594, compound

Product 1

HCID 10107310HCID 10107310, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methyl-3,4,5,6-tetrahydro-2H-benzo[e][1,4]diazocin-1-ylamine (1.50 g, 8.1 mmole) in 1-propanol (100 mL) was added tetrahydro-thiopyran-4-one (5.0 g, 43 mmole), followed by p-toluenesulfonic acid monohydrate (3.2 g, 16.8 mmole), and the resulting reaction mixture was refluxed for 40 hours. The reaction mixture was cooled to room temperature and solvent removed in vacuo to produce a brown residue. The residue was diluted with ethyl acetate (300 mL) and washed with saturated aqueous sodium bicarbonate (150 mL), saturated aqueous sodium chloride (150 mL), dried (sodium sulfate) and concentrated in vacuo. Purification by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1) provided 0.52 g of the title compound as an off-white solid, mp 123-125° C., with a trace of ethyl acetate. MS (ESI) m/z 273 ([M+H]+).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 40 hours
  3. customsolvent removed in vacuo
  4. customto produce a brown residue
  5. washwashed with saturated aqueous sodium bicarbonate (150 mL), saturated aqueous sodium chloride (150 mL)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customPurification by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1)

Sources & evidence

ORD record
ord-4ef3c8fc5dd041cbad809f5288198cf0
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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