Water → N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-N-(2-phenylaminoethyl)-methylamine

HRID 364074Notes

Reaction equation

HRID 364074 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.[C:21]1([NH:27][CH2:28][CH2:29][NH:30][CH3:31])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(OCC)C>[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:30]([CH3:31])[CH2:29][CH2:28][NH:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10582940Methyl[2-(phenylamino)ethyl]amineHCID 130925103-(3-Chloropropyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Product 1

HCID 13579666N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-N-(2-phenylaminoethyl)-methylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Here, 3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-1-chloropropane (9 g, 0.0336 mol) is heated to 130° C. for 30 minutes with N-(2-phenylaminoethyl)-methylamine (11 g, 0.073 mol). After cooling, the reaction mixture is distributed between water and diethylether. The organic phase is separated, dried over sodium sulfate and concentrated by evaporation. The residue is recrystallized from toluene/petroleum ether.

Workup

  1. temperatureAfter cooling
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is recrystallized from toluene/petroleum ether

Sources & evidence

ORD record
ord-cec3cf093d2642b99435172808ba3265
Source dataset
uspto-grants-1986_08
Patent number
US04604389

Reaction notes

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