Potassium Carbonate → 4-{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}-morpholine

HRID 272884Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][NH2:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:25][CH2:26][O:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][N:23]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of {4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (207 mg, 0.65 mmol) and bis(2-bromoethyl)ether (82 μL, 1.3 mmol) in anhydrous acetonitrile (10 mL) was added potassium carbonate (180 mg, 1.3 mmol). The mixture was heated to 60° C. overnight then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with DCM:MeOH (97:3) with 10% NH3 to give the title compound (90 mg, 23% yield).

Workup

concentrationthen concentrated under reduced pressure
customThe crude product was purified by column chromatography on silica gel eluting with DCM:MeOH (97:3) with 10% NH3

Sources & evidence

ORD record: ord-fb6aa859a8ba491d9c688a79143897d9
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

Loading…