Morpholine → HCID 12043587, compound

HRID 394004Notes

Reaction equation

HRID 394004 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH2:10])[CH:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.O1CCOC[CH2:24]1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:24][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:3]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 312751,4-DioxaneHCID 110746614-methyl-2-(1-phenyl-vinyl)-phenol

Product 1

HCID 12043587HCID 12043587, compoundYield 82%

Procedure

0.421 g (2.0 mmole) 4-methyl-2-(1-phenyl-vinyl)-phenol, 0.10 ml (1.15 mmole) morpholine, 6.0 mg (12 μmole) [RhCl(cod)]2 and 10 ml abs. dioxane are agitated in a pressure vessel for 3 days at 120° C. and under a pressure of 90 bar synthesis gas (CO:H2=7.2). Following cooling and relieving of the pressure vessel, the reaction solution undergoes absorptive filtering (eluant: diethylether, then ethanol) through aluminium oxide (activity II-III, basic). Following removal of the solvent, the cleaning of the raw product takes place by column chromatography on silica gel with cyclohexane/MTBE (ratio of volumes=1/1) as the eluant. 255 mg (0.82 mmole, 82%) 4-methyl-2-(3-morpholin-4-yl-1-phenyl-propyl)-phenol are obtained.

Workup

  1. temperatureFollowing cooling
  2. filtrationthe reaction solution undergoes absorptive filtering (eluant
  3. customremoval of the solvent

Sources & evidence

ORD record
ord-227ea79621964436afdc5f1826554f6c
Source dataset
uspto-grants-2004_10
Patent number
US06809225B2

Reaction notes

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