4-(2-Propyn-1-yl)morpholine → HCID 131728889, compound

HRID 549916Notes

Reaction equation

HRID 549916 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)[C:2]#[CH:3].Br[C:11]1[CH:16]=[CH:15][C:14](/[C:17](/[C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)=[CH:18]/[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:23]([CH3:34])[CH:22]=2)=[CH:13][CH:12]=1>C(N(CC)CC)C.C1C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:41][C:38]1[CH:37]=[CH:36][C:35](/[C:17](/[C:14]2[CH:13]=[CH:12][C:11]([C:3]#[C:2][CH2:1][N:4]3[CH2:9][CH2:8][O:7][CH2:6][CH2:5]3)=[CH:16][CH:15]=2)=[CH:18]\[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:23]([CH3:34])[CH:22]=2)=[CH:40][CH:39]=1

Participants

6

Reactant 2

HCID 4129414-(2-Propyn-1-yl)morpholineHCID 131728890HCID 131728890, compound

Product 1

HCID 131728889HCID 131728889, compound

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

Under nitrogen atmosphere, 4-propargylmorpholine (550 mg, 4.4 mmol) bis(triphenylphosphine)palladium(II) dichloride (40 mg, 0.057 mmol) and copper(II) acetate (7 mg, 0.038 mmol) were added to a degassed solution of the above ester (280 mg, 0.55 mmol) in triethylamine (30 mL). The reaction mixture was refluxed for 8 h, diluted with benzene (100 mL), filtered and evaporated in vacuo. The residue was purified by column chromatography (silica gel Fluka 60, chloroform/methanol 9:1) yielding ethyl (Z)-[4-[3-(4-chlorophenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]allyloxy]-2-methylphenyl]propionate.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography (silica gel Fluka 60, chloroform/methanol 9:1)

Sources & evidence

ORD record
ord-65412f3688d14d7d9ee0860819afa798
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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