Potassium Iodide → HCID 59352467, compound

HRID 1407796Notes

Reaction equation

HRID 1407796 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2([C:23]3[C:14](=[CH:15][C:16]4[O:21][CH2:20][CH2:19][O:18][C:17]=4[CH:22]=3)[O:13][CH2:12]2)[C:4]1=[O:24].[CH2:25]([N:32]1[CH2:37][CH2:36][O:35][CH:34]([CH2:38]Cl)[CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[I-].[K+]>CN(C)C=O>[CH2:25]([N:32]1[CH2:37][CH2:36][O:35][CH:34]([CH2:38][N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]3([C:23]4[C:14](=[CH:15][C:16]5[O:21][CH2:20][CH2:19][O:18][C:17]=5[CH:22]=4)[O:13][CH2:12]3)[C:4]2=[O:24])[CH2:33]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 28015624-Benzyl-2-(chloromethyl)morpholineHCID 58224164Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydro

Product 1

HCID 59352467HCID 59352467, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of sodium hydride (60% w/w dispersion in mineral oil, 0.48 g, 12 mmol) in N,N-dimethylformamide (10 mL) at 0° C. was added 2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (2.95 g, 10 mmol). The reaction mixture was stirred for 30 min and 4-benzyl-2-(chloromethyl)morpholine (2.71 g, 12 mmol) and potassium iodide (0.10 g, 0.60 mmol) were added. The reaction mixture was heated at 100° C. for 16 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography and eluted with ethyl acetate/hexanes (3/7) to afford 1′-[(4-benzylmorpholin-2-yl)methyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.75 g, 74%) as a colorless solid: mp 88-100° C.; 1H NMR (mixture of diasteroisomers, 300 MHz, CDCl3) δ7.35-7.20 (m, 6H), 7.16-7.11 (m, 1H), 7.07-7.00 (m, 2H), 6.48 (s, 1H), 6.25 (s, 0.5H), 6.20 (s, 0.5H), 4.90-4.80 (m, 1H), 4.64-4.57 (m, 1H), 4.22-4.08 (m, 4H), 3.98-3.40 (m, 7H), 2.87-2.56 (m, 2H), 2.23-1.98 (m, 2H); MS (ES+) m/z 485.0 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography
  4. washeluted with ethyl acetate/hexanes (3/7)

Sources & evidence

ORD record
ord-e458e0cbd84e467f9cf42307ce273861
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…