Triethylamine → HCID 18995772, compound

HRID 1768970Notes

Reaction equation

HRID 1768970 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-599a348edcd94a1988984daf61766cf7
Source dataset
uspto-grants-1995_01
Patent number
US05380725

Reaction notes

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