Triethylamine → HCID 178487527, compound

HRID 34996Notes

Reaction equation

HRID 34996 reaction equation
N#N.[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([S:15]([NH:18][C@H:19]([C:27](Cl)=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])(=[O:17])=[O:16])=[CH:12]2)=[CH:7][CH:6]=1.Cl.Cl.[Cl:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([S:15]([NH:18][C@H:19]([C:27]([N:42]3[CH2:41][CH2:40][N:39]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[Cl:32])[CH2:44][CH2:43]3)=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])(=[O:16])=[O:17])=[CH:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30186831-(2-Chlorophenyl)piperazine dihydrochlorideHCID 178487526HCID 178487526, compound

Product 1

HCID 178487527HCID 178487527, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The thus obtained N2 -(7-methoxy-2-naphthalene-sulfonyl)-L-arginyl chloride (2.4 g) is immediately added to a solution of 1.64 g (0.00608 mole) 1-(2-chlorophenyl)piperazine dihydrochloride and 2.56 g (0.0253 mole) triethylamine in 50 ml chloroform under ice chilling. After 10 minutes, the mixture is brought to room temperature, and allowed to stand overnight. Then the reaction mixture is washed with water and the solvent is distilled off. The residue is washed with ethyl ether and dissolved in a 30%-ethanol/50 ml water mixture, and made basic with a 2N sodium hydroxide aqueous solution to pH 10. Thus an oily substance is deposited and is crystallized on standing. The crystals are collected by filtration, dried, and recrystallized from 20 ml THF, and 0.83 g of 1-[N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginyl]-4-(2-chlorophenyl)piperazine is obtained. Yield 28%. m.p. 219°~221° C. (decomp.) IR(KBr): 3330, 1625, 1480 cm-1.

Workup

  1. customis brought to room temperature
  2. waitto stand overnight
  3. washThen the reaction mixture is washed with water
  4. distillationthe solvent is distilled off
  5. washThe residue is washed with ethyl ether
  6. dissolutiondissolved in a 30%-ethanol/50 ml water mixture
  7. customis crystallized
  8. filtrationThe crystals are collected by filtration
  9. customdried
  10. customrecrystallized from 20 ml THF

Sources & evidence

ORD record
ord-e2392e9df97544ac878ce9a5ccfd728a
Source dataset
uspto-grants-1988_08
Patent number
US04764618

Reaction notes

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