Triethylamine → N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]4-nitrobenzamide hydrochloride

HRID 1601339Notes

Reaction equation

HRID 1601339 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][NH2:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([Cl:28])=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].C(N(CC)CC)C>C(Cl)Cl>[ClH:28].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][NH:17][C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 104449491,3-Propanediamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-

Product 1

HCID 70011353N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]4-nitrobenzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

800 mg (3.17 mmol) N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methyl-1,3-propanediamine (D2), 630 mg (3.33 mmol) 4-nitro benzoyl chloride and 0.35 g (3.49 mmol) triethylamine in 30 ml methylene chloride were stirred for 2 hours at room temperature. The mixture was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified twice by chromatography on silicagel using methylene chloride/methanol: 97/3 then 94/6 yielding 700 mg (55%) of the desired compound as a base. The compound was salified in methylene chloride by adding a solution of hydrochoric acid in diethyl ether yielding 594 mg (43%) of the desired compound as a yellow solid: mp=80-90° C.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified twice by chromatography on silicagel
  5. additionby adding a solution of hydrochoric acid in diethyl ether yielding 594 mg (43%) of the desired compound as a yellow solid

Sources & evidence

ORD record
ord-b1c9f2e7e66c4a66b685ac83eedc19ef
Source dataset
uspto-grants-1999_11
Patent number
US05977179

Reaction notes

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