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

HRID 1702101Notes

Reaction equation

HRID 1702101 reaction equation
[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.[Cl:25]C1C=C2N(C3C=CC=CC=3[N+]([O-])=O)CC3(CCN(/C(/C([O-])=O)=C/C([O-])=O)CC3)C2=CC=1.C(O)C.Cl>[Fe].O>[ClH:1].[ClH:25].[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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 128016306-Chloro-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]HCID 88734204HCID 88734204, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-653966e5a4d74636b85166ae40b687d7
Source dataset
uspto-grants-1983_04
Patent number
US04379933

Reaction notes

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