N-Methylhomoveratrylamine → HCID 86739858, compound

HRID 1154640Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14][Cl:15])[CH:10]=[CH:11][C:5]=2[CH:4]=1.CNCCC1C=CC(OC)=C(OC)C=1>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[NH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1.[ClH:15].[CH3:10][N:9]([CH2:12][CH2:13][CH3:14])[CH2:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:18]([O:19][CH3:20])[CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5.9 gm (0.02 mol) of 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl) -3-chloro propane and 11.7 gm (0.0006 mol) of N-methyl-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine was heated at 100° C. for 3 hours, then cooled and dissolved in ethyl acetate/water. The organic phase was removed, washed three times with 1% acetic acid and extracted by shaking twice with 2N hydrochloric acid. The hydrochloric acid extract was made alkaline with ammonia and extracted with methylene chloride. The solvent of the extract was removed in vacuo; the residue was dissolved in acetone, and the hydrochloride was precipitated with ethereal hydrochloric acid.

Workup

temperaturecooled
customThe organic phase was removed
washwashed three times with 1% acetic acid
extractionextracted
extractionThe hydrochloric acid extract
extractionextracted with methylene chloride
customThe solvent of the extract was removed in vacuo
dissolutionthe residue was dissolved in acetone
customthe hydrochloride was precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record: ord-dd594bf73fbb42508c9e9538e281e725
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04490369

Reaction notes

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