Morpholine → HCID 59352469, compound

HRID 1965693Notes

Reaction equation

HRID 1965693 reaction equation
Br[C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]3([CH2:19][O:18][C:17]4[CH:20]=[C:21]5[C:25](=[CH:26][C:16]3=4)[CH2:24][CH2:23][O:22]5)[C:8]2=[O:27])=[CH:4][CH:3]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cu]=O>[N:30]1([C:2]2[CH:29]=[CH:28][C:5]([CH2:6][N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]4([CH2:19][O:18][C:17]5[CH:20]=[C:21]6[C:25](=[CH:26][C:16]4=5)[CH2:24][CH2:23][O:22]6)[C:8]3=[O:27])=[CH:4][CH:3]=2)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 68596795HCID 68596795, compound

Product 1

HCID 59352469HCID 59352469, compound

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
130 °C

Procedure

A suspension of 1′-(4-bromobenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.45 g, 1.0 mmol), morpholine (0.26 g, 3.0 mmol), dicyclohexyloxalylhydrazide (0.14 g, 0.5 mmol), tetrabutylammonium bromide (0.34 g, 1 mmol), copper (II) oxide (0.05 g, 0.6 mmol) and cesium carbonate (0.65 g, 2.0 mmol) was heated in microwave reactor at 130° C. for 10 min. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to column chromatography with dichloromethane-methanol (100:1-10:1) to afford 1′-(4-morpholin-4-ylbenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.35-6.74 (m, 8H), (0.09 g, 19%), 6.45 (s, 1H), 6.41 (s, 1H), 4.87 (ABq, 2H), 4.81 (ABq, 2H), 4.52 (t, J=8.7, 8.7 Hz, 2H), 4.01-3.74 (m, 4H), 3.25-3.07 (m, 4H), 3.05-2.90 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 177.8, 161.8, 161.3, 142.1, 132.8, 128.6 (2C), 123.8, 123.3, 120.2, 119.9, 118.9, 116.0, 109.3, 93.2, 80.6, 72.3, 66.6, 57.7, 49.4, 43.6, 29.0; MS (ES+) m/z 454.87 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b05fb3e261954db79323b6ea2990cb7f
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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