Sodium Hydroxide → 1-[4-(4-Chlorobenzyl)-1-piperazinyl]-3-[4-(2-carboxy-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride

HRID 4321노트

반응식

HRID 4321 반응식
[ClH:1].Cl.Cl.Cl.[Cl:5][C:6]1[CH:40]=[CH:39][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH:27]([C:34]([O:36]CC)=[O:35])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:22][CH2:21]3)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)C>[ClH:5].[ClH:1].[ClH:5].[ClH:5].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][N:23]([CH2:26][CH:27]([C:34]([OH:36])=[O:35])[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:24][CH2:25]3)[CH2:13][CH2:12]2)=[CH:39][CH:40]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 201522231-[4-(4-Chlorobenzyl)-1-piperazinyl]-3-[4-(2-ethoxycarbonyl-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride

생성물 1

HCID 201522421-[4-(4-Chlorobenzyl)-1-piperazinyl]-3-[4-(2-carboxy-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride수율 172%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of 340 mg of 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-[4-(2-ethoxycarbonyl-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride in 10 ml of ethanol was treated with 1 ml of aqueous 5M sodium hydroxide and heated under reflux for 1 hour. The reaction mixture was evaporated to dryness under reduced pressure. The residue was mixed with lN hydrochloric acid (3 ml) and the resulting mixture extracted with ether (2×10 ml). The extract was discarded and the pH of aqueous phase adjusted to 5.5 with 1N hydrochloric acid. Aqueous saturated sodium chloride solution (10 ml) was added and the mixture extracted with butanol (2×10 ml). The butanol extract was filtered and treated with excess ethereal hydrogen chloride. The white precipitate was collected and recrystallized from aqueous ethanol to yield 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-[4-(2-carboxy-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride (140 mg, 40% yield) as a white crystalline solid (m.p. 230°-245° C. decomp.).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customThe reaction mixture was evaporated to dryness under reduced pressure
  4. additionThe residue was mixed with lN hydrochloric acid (3 ml)
  5. extractionthe resulting mixture extracted with ether (2×10 ml)
  6. additionAqueous saturated sodium chloride solution (10 ml) was added
  7. extractionthe mixture extracted with butanol (2×10 ml)
  8. extractionThe butanol extract
  9. filtrationwas filtered
  10. additiontreated with excess ethereal hydrogen chloride
  11. customThe white precipitate was collected
  12. customrecrystallized from aqueous ethanol

출처 및 근거

ORD 기록
ord-13fda9fea57447eebddeaa653b8ac3a5
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725597

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