Triethylamine → 2-[4-(2-(1,3-Dioxolan-2-yl)-ethyl)-1-piperazinyl]-1-phenyl indole 3-carboxylic acid (4-methyl)-piperazide

HRID 26208Notes

Reaction equation

HRID 26208 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:9])[CH2:4][CH2:3]1.Cl[CH2:32][CH2:33][CH:34]1[O:38][CH2:37][CH2:36][O:35]1.C(N(CC)CC)C.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[N:25]2[CH2:26][CH2:27][N:28]([CH2:32][CH2:33][CH:34]3[O:38][CH2:37][CH2:36][O:35]3)[CH2:29][CH2:30]2)=[O:9])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 780712-(2-Chloroethyl)-1,3-dioxolaneHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 867364551-Phenyl-2-(1-piperazinyl)-indole 3-carboxylic acid (4-methyl)-Piperazide

Product 1

HCID 867364582-[4-(2-(1,3-Dioxolan-2-yl)-ethyl)-1-piperazinyl]-1-phenyl indole 3-carboxylic acid (4-methyl)-piperazide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

A stirred mixture of 8 g (0.02 mol) of 1-phenyl-2-(1-piperazinyl)-indole 3-carboxylic acid (4-methyl)-piperazide, 9.45 g (0.07 mol) of 2-(2-chloroethyl)-1,3-dioxolane and 9.7 ml of triethylamine in 60 ml of toluene was maintained at the boil for 40 hours. After cooling, the mixture was diluted with 200 ml of chloroform, washed three times with water, and the solvent was eliminated in vacuo. The resinous residue of the organic phase was chromatographed using silica gel 60 (0.06-0.2 mm, deactivated by 10% of water, column size: 3 × 100 cm) with chloroform containing 10% methanol. The base was eluted as a resin. The yield amounted to 6.6 g (66% of the theoretical yield). The dihydrochloride melted at 215°-217° C.

Workup

  1. temperaturewas maintained at the boil for 40 hours
  2. temperatureAfter cooling
  3. washwashed three times with water
  4. customThe resinous residue of the organic phase was chromatographed
  5. washThe base was eluted as a resin
  6. customtheoretical yield)

Sources & evidence

ORD record
ord-2ea726274d5b438283d3b7d1fe3bc327
Source dataset
uspto-grants-1979_04
Patent number
US04148895

Reaction notes

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