Hydrochloric Acid → 1-(2-Aminophenyl)-6-chlorospiro[indoline-3,4'-piperidine]dihydrochloride

HRID 1707123노트

반응식

HRID 1707123 반응식
[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-])=O)[CH2:9][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.C(O)(=O)/C=C\C(O)=O.[Cl:33]C1C=C2N(C3C=CC=CC=3[N+]([O-])=O)CC3(CCNCC3)C2=CC=1.C(O)C.Cl>[Fe].O>[ClH:1].[ClH:33].[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:8]1[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=2)[C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:9]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 128016306-Chloro-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]HCID 70510514HCID 70510514, 화합물

생성물 1

HCID 128016321-(2-Aminophenyl)-6-chlorospiro[indoline-3,4'-piperidine]dihydrochloride

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

A mixture of 2.1 g of 6-chloro-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine], free base of Example 33, 95 ml of 95% ethyl alcohol, 7.5 ml of water and 4.4 g of iron powder is acidified with 0.2 ml of concentrated hydrochloric acid and then refluxed under nitrogen for 10 minutes. Thereafter, the mixture is permitted to cool before being filtered through celite. The filtrate is concentrated under vacuum leaving an oily residue which is basified. The alkaline mixture is extracted with ether and then dried. The product is converted to a solid dihydrochloric acid salt which is recrystallized from a methyl alcohol-ether mixture to provide off-white prisms, mp 270°-273° C. (after darkening) of 1-(2-aminophenyl)-6-chlorospiro[indoline-3,4'-piperidine]dihydrochloride.

후처리

  1. temperaturerefluxed under nitrogen for 10 minutes
  2. temperatureto cool
  3. filtrationbefore being filtered through celite
  4. concentrationThe filtrate is concentrated under vacuum
  5. customleaving an oily residue which
  6. extractionThe alkaline mixture is extracted with ether
  7. customdried
  8. customis recrystallized from a methyl alcohol-ether mixture

출처 및 근거

ORD 기록
ord-571ea8d7ac2141aca1cd85a324dcf952
출처 데이터셋
uspto-grants-1980_06
특허 번호
US04209625

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