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Triethylamine → HCID 13319934, compound

HRID 1154682
Notes
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Reaction equation

HRID 1154682 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7131256N-[3-(3,4-dimethoxyphenyl)propyl]-N-methylamineHCID 130925103-(3-Chloropropyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Product 1

HCID 13319934HCID 13319934, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent
HCID 21908982
Water methylene chloride
Solvent

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

  1. temperaturecooled
  2. customThe organic phase was separated
  3. extractionextracted with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation in vacuo
  6. customthe residue was purified on silica gel
  7. customThe oily free base product thus obtained
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes