N,N'-Dimethylethylenediamine → HCID 71599013, compound

HRID 925626Notes

Reaction equation

[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C[N:20]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21]1.[CH3:28]NCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu](I)I.C(Cl)(Cl)Cl>[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N:20]4[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21]4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 1-cyclobutyl-4-(4-iodophenoxy)piperidine (3 g; can be synthesized in accordance with the method described in WO2008072703), methyl 1H-pyrrole-3-carboxylic acid (1.75 g), N,N′-dimethylethylenediamine (0.592 g), copper iodide (0.32 g) and cesium carbonate (2.32 g) in toluene (8.4 mL) was stirred at 110° C. for 4 hours. The reaction mixture was left to cool to room temperature and, after adding chloroform, filtered through Celite (registered trademark). The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (NH form silica gel; eluent: n-hexane/ethyl acetate=88/12-0/100) to give the titled compound as a colorless solid (1.42 g).

Workup

customcan be synthesized in accordance with the method
waitThe reaction mixture was left
temperatureto cool to room temperature
filtrationfiltered through Celite (registered trademark)
concentrationThe filtrate was concentrated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (NH form silica gel; eluent: n-hexane/ethyl acetate=88/12-0/100)

Sources & evidence

ORD record: ord-31d8867a572f49cd99d12ce9673aa2bf
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284324B2

Reaction notes

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