Morpholine → HCID 68359225, compound

HRID 339900Notes

Reaction equation

HRID 339900 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C.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]>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][S:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:3][CH:4]=1)(=[O:11])=[O:10]

Participants

7

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 68292190HCID 68292190, compound

Product 1

HCID 68359225HCID 68359225, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of C-(4-bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide (1 g), morpholine (0.3 ml), Pd2(dba)3 (51 mg) and cesium carbonate (1.3 g) in dioxane was stirred at 80° C. for 16 h. The mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated. This was followed by purification by column chromatography (ethyl acetate/heptane). This gave the product (267 mg) with a molecular weight of 406.5 g/mol (C20H26N2O5S).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThis was followed by purification by column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-668d0254a0b149da8e99ea3121eb9915
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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