N-Methylethylamine → HCID 68645089, compound

HRID 1160495Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1.[OH-].[Na+].[CH3:18][NH:19][CH2:20][CH3:21]>O>[CH3:18][N:19]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[CH2:20][CH3:21]

Participants

Conditions

Temperature: 40 °C

Procedure

A 100 mL flask provided with a stirrer and a reflux condenser was charged in a nitrogen gas atmosphere with 14.6 g (0.05 mol) of the p-(6-chlorohexyloxy)bromobenzene, synthesized at the above-mentioned step 1), 4.0 g (0.10 mol) of sodium hydroxide (available from Wako Pure Chemical Industries Ltd.), 0.8 g (0.012 mol) of n-tetrabutylammonium bromide (available from Kanto Chemical Co., Inc.) and 5.0 g of water. The content was maintained at 40° C. while being stirred. Then 5.9 g (0.10 mol) of methylethylamine (available from Wako Pure Chemical Industries Ltd.) was dropwise added at the same temperature over a period of 2 hours. Thereafter the reaction liquid was maintained at that temperature for 20 hours while being stirred. After completion of the reaction, the phase separation was conducted and the organic phase was subjected to silica-gel column chromatography to give 13.4 g of the target p-(N-methyl-N-ethylaminohexyloxy)bromobenzene (yield: 80%, purity: 94%).

Workup

customA 100 mL flask provided with a stirrer and a reflux condenser
customThereafter the reaction liquid
temperaturewas maintained at that temperature for 20 hours
stirringwhile being stirred
customAfter completion of the reaction
customthe phase separation

Sources & evidence

ORD record: ord-dfbb337c5eef4250ae23e91d1c89ac6c
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816475B2

Reaction notes

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