Potassium Carbonate → HCID 21959415, compound

HRID 557373Notes

Reaction equation

HRID 557373 reaction equation
C([O-])([O-])=O.[K+].[K+].[N+:7]([C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[CH:15][NH:16]2)=[CH:12][CH:11]=1)([O-])=O.Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CC#N>[N:23]1([CH2:22][CH2:21][N:16]2[C:17]3[C:13](=[CH:12][CH:11]=[C:10]([NH2:7])[CH:18]=3)[CH:14]=[CH:15]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 785026-Nitro-1H-indole

Product 1

HCID 21959415HCID 21959415, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

K2CO3 (5.08 g, 36.726 mmol) was added to a slurry of 6-nitroindole (1.985 g, 12.242 mmol), 4-(2-chloroethyl)morpholine hydrochloride (2.278 g, 12.242 mmol), and CH3CN (100 ml). The mix was heated at reflux for 18 h, then cooled to RT, filtered, and concentrated in vacuo. The crude was eluted through a silica gel column with a gradient of 3:97 to 5:95 and finally 8:92 MeOH:CH2Cl2, to yield upon drying 1-(2-morpholin-4-yl-ethyl)-6-nitro-1H-indole which was hydrogenated at regular condition described early to yield the title compound.

Workup

  1. temperatureThe mix was heated
  2. temperatureat reflux for 18 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe crude was eluted through a silica gel column with a gradient of 3:97 to 5:95 and finally 8:92 MeOH
  6. customCH2Cl2, to yield
  7. dry with materialupon drying 1-(2-morpholin-4-yl-ethyl)-6-nitro-1H-indole which

Sources & evidence

ORD record
ord-5895e569ce894f8592ab4fe4af25d096
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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