Triethylamine → HCID 57662029, compound

HRID 1665350Notes

Reaction equation

HRID 1665350 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(#N)C>[C:33]1([CH2:32][CH2:31][CH2:30][N:1]2[CH2:2][CH2:3][C:4]3([O:11][C:10]4[C:12]5[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=4[S:8][CH2:7]3)=[CH:16][CH:15]=[CH:14][CH:13]=5)[CH2:5][CH2:6]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzeneHCID 57661820Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 57662029HCID 57662029, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione (0.566 g, 1.88 mmol) in acetonitrile (30 mL) was added triethylamine (0.80 mL, 5.64 mmol) followed by (3-bromopropyl)benzene (0.747 g, 3.76 mmol). The reaction was stirred at 70° C. for 3 hours. The solvent was then evaporated under reduced pressure. The residue was dissolved in dichloromethane (30 mL) and the organic layer was washed with water (30 mL). The organic extract was dried with Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatorgraphy (SiO2, 8% CH3OH in dichloromethane). The product obtained after the chromatography was further purified by crystallization from hexanes and dichloromethane to give the desired product as a purple solid (0.405 g, 51%). M.p.=112-114° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.90 (d, J=7.6 Hz, 1H), 7.78 (d, J=3.2 Hz, 2H), 7.58-7.54 (m, 1H), 7.29-7.22 (m, 2H), 7.21-7.14 (m, 3H), 3.07 (s, 2H), 2.74 (m, 2H), 2.60 (t, J=7.6 Hz 2H), 2.37-2.27 (m, 4H), 2.05-1-97 (m, 2H), 1.85-1.71 (m, 4H); LCMS: 420 [M+H]; Calc. for C25H25NO3S: C 71.51, H 6.005, N 3.338; Found C 72.08, H 5.35, N 3.43.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (30 mL)
  3. washthe organic layer was washed with water (30 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatorgraphy (SiO2, 8% CH3OH in dichloromethane)
  8. customThe product obtained after the chromatography
  9. customwas further purified by crystallization from hexanes and dichloromethane

Sources & evidence

ORD record
ord-629c4862799e44e3a37bc9b9dc030b02
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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