Nitrogen → 5-(Morpholin-4-yl)-2,3-dihydro-1H-inden-1-one

HRID 2252259Notes

Reaction equation

HRID 2252259 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C([O-])([O-])=O.[Cs+].[Cs+].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.N#N>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[N:18]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 947NitrogenHCID 8083MorpholineHCID 10796Cesium carbonateHCID 5206955-Bromo-1-indanone

Product 1

HCID 461728755-(Morpholin-4-yl)-2,3-dihydro-1H-inden-1-oneYield 51.1%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromo-1-indanone (0.76 g, 3.60 mmol), Cs2CO3 (1.64 g, 5.04 mmol), Pd2(dba)3 (82 mg, 0.09 mmol), BINAP (112 mg, 0.18 mmol), morpholine (0.94 mL, 10.8 mmol) and THF (15 ml) was pumped with N2 for 0.5 hour and then heated to reflux overnight. The reaction mixture was concentrated, and purified by flash chromatography to give the above intermediate (0.40 g, 51.1%). MS (ESI) m/z 218 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 2.59-2.65 (m, 2H) 3.03-3.10 (m, 2H) 3.34-3.40 (m, 4H) 3.79-3.85 (m, 4H) 6.95 (s, 1H) 6.99 (m, 1H) 7.57 (d, J=8.48 Hz, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-686ca8493f3e4fecaca6a4fd51cb9f66
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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