Potassium Carbonate → HCID 57447695, compound

HRID 1669209Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6].Br[CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2[C:13](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]1=[O:21]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 2-methoxy-N-methylethanamine (266) (20.0 g, 224 mmol), N-(3-bromopropyl)phthalimide (50.1 g, 187 mmol) and K2CO3 (31.0 g, 224 mmol) in DMF (200 mL) was stirred at 100° C. for 3 h. The solution was cooled and the solvent evaporated to give phthalimide 298 (51.7 g, 100%) as a colourless oil, which was used without further purification: 1H NMR δ 7.82-7.86 (m, 2H, Harom), 7.68-7.73 (m, 2H, Harom), 3.73 (t, J=7.2 Hz, 2H, CH2N), 3.42-3.46 (m, 2H, CH2O), 3.32 (s, 3H, OCH3), 2.53-2.56 (m, 2H, CH2N), 2.44-2.49 (m, 2H, CH2N), 2.25 (s, 3H, NCH3), 1.82-1.90 (m, 2H, CH2); HRMS (Cl+) calcd for C15H21N2O3 (MH+) m/z 277.1552, found 277.1557.

Workup

temperatureThe solution was cooled
customthe solvent evaporated

Sources & evidence

ORD record: ord-5c73196bd4d3467e8ec320ca07c5e365
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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