Hydrochloric Acid → HCID 59441889, compound

HRID 1014326Notes

Reaction equation

HRID 1014326 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:26][CH3:27])=[C:20]([N+:23]([O-])=O)[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH2:6][CH2:5]1)[CH3:3].O.O.[Sn](Cl)Cl.Cl>C(O)C.CC(N(C)C)=O>[CH3:3][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:26][CH3:27])=[C:20]([NH2:23])[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH2:6][CH2:5]1)[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 59441931HCID 59441931, compound

Product 1

HCID 59441889HCID 59441889, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 1-{3-[4-(1-methylethyl)-1-piperazinyl]propanoyl}-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (0.62 g, 1.65 mmol) in absolute ethanol (150 mL) and DMA (10 mL) was added tin (II) chloride dihydrate (2.23 g, 7.84 mmol) and 1M HCl(3.0 mL). After overnight stirring, reaction was quenched with excess saturated NaHCO3 solution, stirred for one hr, and filtered through a celite pad which was rinsed with methanol. After organic solvent removal, the aqueous layer was extracted with dichloromethane (2×200 mL), the organic layers were combined, adsorbed to silica gel and purified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH) to afford 1-{3-[4-(1-methylethyl)-1-piperazinyl]propanoyl}-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine. ESIMS (M+H)+=347.

Workup

  1. customreaction
  2. customwas quenched with excess saturated NaHCO3 solution
  3. stirringstirred for one hr
  4. filtrationfiltered through a celite pad which
  5. washwas rinsed with methanol
  6. customAfter organic solvent removal
  7. extractionthe aqueous layer was extracted with dichloromethane (2×200 mL)
  8. custompurified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH)

Sources & evidence

ORD record
ord-12e628b24a6b46a7b4f695ab0ce6b1e6
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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