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

HRID 1660360ノート

反応式

HRID 1660360 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fe8685253d7444c6bfb7575572128698
出典データセット
uspto-grants-1981_12
特許番号
US04307235

反応ノート

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