1-(2-Methoxyphenyl)piperazine → HCID 23369828, compound

HRID 1900753Notes

Reaction equation

HRID 1900753 reaction equation
Br[CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(Cl)(Cl)Cl.CO>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH:3]2[O:17][C:6]3=[C:7]4[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]3[CH2:4]2)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]4)[CH2:28][CH2:27]1

Participants

5

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 233696452-Bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 23369828HCID 23369828, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (3.824 g) and 1-(2-methoxyphenyl)piperazine (5.000 g) was stirred in a hot bath at 150° C. in the stream of argon gas for 1 hour. The reaction product was dissolved in a solvent mixture of chloroform and methanol (5:1), and washed with sodium bicarbonate water, and water in this order. After dried and condensed, n-hexane was added to the residue, and the mixture was allowed to stand. As a result, 4.349 g of a free base of the title compound was obtained as pale yellow flakes (mp.: 245°-247° C. (dec.)).

Workup

  1. washwashed with sodium bicarbonate water, and water in this order
  2. customAfter dried
  3. customcondensed, n-hexane
  4. additionwas added to the residue

Sources & evidence

ORD record
ord-ea8940eef8c443988609eb0a3096e23b
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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