Sodium Iodide → 2-(4-Octyloxy-phenyl)-4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-morpholine

HRID 2167908Notes

Reaction equation

[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[CH2:23][CH2:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[CH2:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[O:21][CH2:20][CH2:19][N:18]([CH2:23][CH2:24][O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[CH2:17]2)=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(4-octyloxy-phenyl)-morpholine (1.99 g; 6.8 mmol), 2-(2-chloroethoxy)-tetrahydro-2H-pyran (1.21 ml; 8.2 mmol), K2CO3 (1.89 g; 13.7 mmol) and NaI (0.20 g; 1.4 mmol) in DMF (15 mL) was heated to 100° C. overnight. After cooling to RT the reaction mixture was partitioned between 5% aqueous NaHCO3 solution and Et2O. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, EtOAc) to afford 2-(4-octyloxy-phenyl)-4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-morpholine (2.04 g).

Workup

temperatureAfter cooling to RT the reaction mixture
customwas partitioned between 5% aqueous NaHCO3 solution and Et2O
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2, EtOAc)

Sources & evidence

ORD record: ord-b7e69bd5574649a291bb39ce2aeabc94
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045441B2

Reaction notes

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