Sodium Hydroxide → N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-2-(3,4-dimethoxyphenylamino)-ethylamine

HRID 364073Notes

Reaction equation

HRID 364073 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)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH:31][CH2:32][CH2:33][NH2:34])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30].[OH-].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(Cl)Cl>[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][NH:34][CH2:33][CH2:32][NH:31][C:25]3[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 130925103-(3-Chloropropyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-oneHCID 135796642-(3,4-Dimethoxyphenylamino)-ethylamine

Product 1

HCID 13579665N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-2-(3,4-dimethoxyphenylamino)-ethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Here, 3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-1-chloropropane (10 g, 0.0336 mol) is heated to 130° C. for 3 hours with 2-(3,4-dimethoxyphenylamino)-ethylamine (13 g, 0.066 mol). After cooling, the reaction mixture is distributed between sodium hydroxide solution and methylene chloride. The organic phase is separated, dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel (eluant: methylene chloride/methanol/conc. ammonia: 90/10/0.25). The product thus obtained is converted into the dihydrochloride in the usual way.

Workup

  1. temperatureAfter cooling
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (eluant: methylene chloride/methanol/conc. ammonia: 90/10/0.25)
  6. customThe product thus obtained

Sources & evidence

ORD record
ord-5ace4c2822404296ac4ec664c4654068
Source dataset
uspto-grants-1986_08
Patent number
US04604389

Reaction notes

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