Ethylene → N-oct-3-en-2-ylmorpholine

HRID 46801Notes

Reaction equation

HRID 46801 reaction equation
Br/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH3:7].[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[C:14]1(C)[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1P([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])C1C=CC=CC=1C.[CH2:36]=[CH2:37]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:2]=[CH:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:9][CH3:10].[CH3:36][CH:37]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[CH:19]=[CH:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:2][CH:28]=[CH:33][CH:32]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[CH2:31][CH2:30][CH2:29][CH3:34]

Participants

9

Reactant 4

HCID 6325EthyleneHCID 8083MorpholineHCID 80271Tri-o-tolylphosphineHCID 6090885cis-1-Bromo-1-hexene

Product 3

HCID 3786404N-oct-2-en-4-ylmorpholineYield 8%HCID 3850183N-oct-3-en-2-ylmorpholineYield 84%HCID 54627001,cis-3-OctadieneYield 5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 10 mmoles cis-1-bromo-1-hexene, 30 mmoles morpholine, 4 ml of acetonitrile, 0.10 mmole palladium acetate and 0.20 mmole of tri-o-tolylphosphine was heated in a pressure vessel under 200 psig of ethylene at 100° C. for 2 hrs. After cooling, the pressure was released and the reaction products were isolated as in Example 1. There was obtained about 5% cis-1,3-octadiene, 84% N-oct-3-en-2-ylmorpholine and 8% N-oct-2-en-4-ylmorpholine.

Workup

  1. temperatureAfter cooling
  2. customthe reaction products were isolated as in Example 1

Sources & evidence

ORD record
ord-9df9a5f124e640b991f8959aab202169
Source dataset
uspto-grants-1979_11
Patent number
US04175187

Reaction notes

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