Sodium Iodide → HCID 68153646, compound

HRID 1946905Notes

Reaction equation

HRID 1946905 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[I-:16].CN[C@@H]1CCCC[C@H]1NC.[I-].[Na+]>O1CCOCC1>[I:16][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 30165Iodide IonHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 581553055-(3-Bromophenyl)-5-methylmorpholin-3-one

Product 1

HCID 68153646HCID 68153646, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (RS)-5-(3-bromo-phenyl)-5-methyl-morpholin-3-one (X-1) (2.0 g), cupper(I) iodide (72 mg), trans-N,N′-dimethyl-1,2-cyclohexandiamine (105 mg), and sodium iodide (2.22 g) in dioxane (20 ml) was heated at 110° C. over the weekend. The reaction mixture was evaporated at reduced pressure and the residue directly transferred to column chromatography on silica using a gradient of dichloromethane/methanol=100/0 to 75/25 as the eluent. The (RS)-5-(3-iodo-phenyl)-5-methyl-morpholin-3-one was obtained as a light green solid (2.26 g, 96% of theory). MS (ISP): m/z=318.2 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated at reduced pressure

Sources & evidence

ORD record
ord-a93aa7fea35e41589b70f05f45a0df54
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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