Homoveratrylamine → HCID 17471905, compound

HRID 1884247Notes

Reaction equation

[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([OH:14])=O.S(Cl)(Cl)=O.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:29][CH2:30][NH2:31])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(N(CC)CC)C>C(OCC)(=O)C.O.O1CCCC1.C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:29][CH2:30][NH:31][C:12](=[O:14])[CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[CH:1]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3.60 g (18.9 mmol) of (5,6,7,8-tetrahydronaphthalen-2-yl)acetic acid, 3.38 g (28.4 mmol) of thionyl chloride and 40 ml of toluene was stirred at 50° C. for 30 minutes and then 80° C. for 2.5 hours, cooled and concentrated under reduced pressure. The residue was added to a mixture of 3.43 g (18.9 mmol) 2-(3,4-dimethoxyphenyl)ethylamine, 2.30 g (22.7 mmol) of triethylamine and 40 ml of tetrahydrofuran at 0° C. and kept at 0° C. for 30 minutes and at room temperature for 3 hours. Water and ethyl acetate were added to the reaction mixture and precipitated solid was collected with filtration. The obtained solid was dried to give 5.78 g of N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acetamide.

Workup

wait80° C. for 2.5 hours
temperaturecooled
concentrationconcentrated under reduced pressure
waitkept at 0° C. for 30 minutes and at room temperature for 3 hours
customprecipitated solid
filtrationwas collected with filtration
customThe obtained solid was dried

Sources & evidence

ORD record: ord-db023ae7ac214aa79b3e2aa78adc3fc7
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762321B2

Reaction notes

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