Triethylamine → HCID 18995772, compound

HRID 1656369Notes

Reaction equation

HRID 1656369 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]1[C:28]([Cl:30])=[O:29].C(N(CC)CC)C>C(Cl)Cl>[OH2:2].[OH2:29].[ClH:30].[ClH:30].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:28]([C:20]2[NH:19][C:27]3[C:22]([CH:21]=2)=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:29])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104672591-(3-Aminopropyl)-4-(2-methoxyphenyl)piperazineHCID 118162081H-indole-2-carbonyl Chloride

Product 1

HCID 18995772HCID 18995772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by stirring [4-(2-methoxyphenyl)piperazino]propylamine (1.4 g, 0.005 mol), indole-2-carboxylic acid chloride (1.0 g, 0.005 mol) and triethylamine (1 g, 0.01 mol) in 50 mL of CH2Cl2 for 24 hours. The methylene chloride solution was washed with water, dried (anhydrous Na2SO4) and evaporated under reduced pressure. The remaining residue was subjected to preparative HPLC over silica gel column and using ethyl acetate as the eluent and the desired product (TLC Rf =0.65 in 30% methanol/ethyl acetate system) was separated and converted to the dihydrochloride dihydrate salt with ethanolic HCl, m.p. 173°-178° C.

Workup

  1. washThe methylene chloride solution was washed with water
  2. dry with materialdried (anhydrous Na2SO4)
  3. customevaporated under reduced pressure
  4. customthe desired product (TLC Rf =0.65 in 30% methanol/ethyl acetate system) was separated

Sources & evidence

ORD record
ord-e2ebb46b75704a40955da57a4a995c7f
Source dataset
uspto-grants-1993_10
Patent number
US05254552

Reaction notes

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