Sodium Hydroxide → HCID 59494650, compound

HRID 872036Notes

Reaction equation

HRID 872036 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]([CH:22]3[CH2:24][CH2:23]3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl.ClC[CH2:28][CH2:29][NH2:30]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[NH2:30][CH2:29][CH2:28][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([CH2:13][N:14]([CH:22]3[CH2:24][CH2:23]3)[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH:8]=2)[C:4]([Cl:3])=[CH:5]1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 114690951-Propanamine, 3-chloro-, hydrochloride2×HCID 86645634HCID 86645634, compound

Product 1

HCID 59494650HCID 59494650, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

Sodium hydroxide (103 mg) and tetrabutylammonium hydrogensulfate (15 mg) were added to a solution of tert-butyl [(3-chloro-1H-indol-6-yl)methyl]cyclopropylcarbamate (275 mg) in acetonitrile (7.0 ml) and the mixture was stirred at room temperature for 20 minutes. 3-Chloropropylamine hydrochloride (149 mg) was added to the reaction mixture and it was heated under reflux for 16 hours. Sodium hydroxide (103 mg) and 3-Chloropropylamine hydrochloride (149 mg) were added and the mixture was further heated to reflux for 2 hours. The reaction mixture was cooled to room temperature, insoluble materials were filtered through Celite and the filtrate was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=20/1 to 10/1) to give tert-butyl {[1-(2-aminoethyl)-3-chloro-1H-indol-6-yl]methyl}cyclopropylcarbamate (257 mg) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. temperaturethe mixture was further heated
  4. temperatureto reflux for 2 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationinsoluble materials were filtered through Celite
  7. additionthe filtrate was diluted with water
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=20/1 to 10/1)

Sources & evidence

ORD record
ord-c662634123414dea86edbdf432cb4fda
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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