2,6-Dichlorophenol → 4-Benzyl-2-[4-(2,6-dichloro-phenoxymethyl)-phenyl]-morpholine

HRID 920549Notes

Reaction equation

HRID 920549 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:43]([N:50]1[CH2:55][CH2:54][O:53][CH:52]([C:56]2[CH:61]=[CH:60][C:59]([CH2:62]O)=[CH:58][CH:57]=2)[CH2:51]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1COCC1>[CH2:43]([N:50]1[CH2:55][CH2:54][O:53][CH:52]([C:56]2[CH:57]=[CH:58][C:59]([CH2:62][O:9][C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])=[CH:60][CH:61]=2)[CH2:51]1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 68992,6-DichlorophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67032692[4-(4-Benzyl-morpholin-2-yl)-phenyl]-methanol

Product 1

HCID 670325914-Benzyl-2-[4-(2,6-dichloro-phenoxymethyl)-phenyl]-morpholineYield 144%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dichlorophenol (0.68 g; 4.19 mmol) in THF (20 mL) was added DIAD (1.13 mL; 5.72 mmol), and triphenylphosphine (1.50 g; 5.72 mmol), at RT, followed, after 30 minutes, by [4-(4-benzyl-morpholin-2-yl)-phenyl]-methanol (1.08 g; 3.81 mmol). Subsequently, the resulting mixture was stirred at RT for 1 hour, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford 4-benzyl-2-[4-(2,6-dichloro-phenoxymethyl)-phenyl]-morpholine (2.35 g) which was used as such in the next step.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1)

Sources & evidence

ORD record
ord-d74531630acc47ae83e0762c79c69f06
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

Loading…