Triethylamine → HCID 13319934, compound

HRID 1154682Notes

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])[CH2:10][CH2:11][C:5]=2[CH:4]=1.C(N(CC)CC)C.[CH3:28][NH:29][CH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[CH:34]=1>C(Cl)Cl.O.CC(C)=O>[ClH:15].[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][N:29]([CH3:28])[CH2:30][CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[CH:34]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 5.55 gm (0.0186 mol) of 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-chloro-propane, 2.6 ml (0.0886 mol) of triethylamine and 3.9 gm (0.0186 mol) of N-methyl-3-(3,4-dimethoxy-phenyl) propylamine was heated at 85° C. for 4 hours, then cooled and dissolved in methylene chloride/water. The organic phase was separated, extracted with water, dried over magnesium sulfate, concentrated by evaporation in vacuo, and the residue was purified on silica gel, using methylene chloride plus 3% ethanol as the eluant. The oily free base product thus obtained was dissolved in acetone, and the hydrochloride was precipitated with ethereal hydrochloric acid.

Workup

temperaturecooled
customThe organic phase was separated
extractionextracted with water
dry with materialdried over magnesium sulfate
concentrationconcentrated by evaporation in vacuo
customthe residue was purified on silica gel
customThe oily free base product thus obtained
customthe hydrochloride was precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record: ord-74f942d0bc2243a392b182cd56219b63
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04490369

Reaction notes

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