Potassium Carbonate → HCID 21959415, compound

HRID 238519Notes

Reaction equation

HRID 238519 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-068301b42b77496b9456ffc4ade57ff3
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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