Sodium Sulfate → 1-{1-[2-(6-Methoxy-1-methyl-1,2,3,4-tetrahydroquinolin-7-yl)ethyl]piperidin-4-yl)-1H-indole-6-carboxamide

HRID 494977Notes

Reaction equation

HRID 494977 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][CH:12](OC)OC)[C:5]([NH2:7])=[O:6].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]1)[N:25]([CH3:38])[CH2:24][CH2:23][CH2:22]2.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.O>[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[CH2:29][CH2:30][N:31]1[CH2:32][CH2:33][CH:34]([N:1]3[C:2]4[C:10](=[CH:9][CH:8]=[C:4]([C:5]([NH2:7])=[O:6])[CH:3]=4)[CH:11]=[CH:12]3)[CH2:35][CH2:36]1)[N:25]([CH3:38])[CH2:24][CH2:23][CH2:22]2

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 576827803-Amino-4-(2,2-dimethoxyethyl)benzamideHCID 576828161-(2-(6-Methoxy-1-methyl-1,2,3,4-tetrahydroquinolin-7-yl)ethyl)piperidin-4-one

Product 1

HCID 576828501-{1-[2-(6-Methoxy-1-methyl-1,2,3,4-tetrahydroquinolin-7-yl)ethyl]piperidin-4-yl)-1H-indole-6-carboxamideYield 54.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

129 mg of 3-amino-4-(2,2-dimethoxyethyl)benzamide and 87 mg of 1-(2-(6-methoxy-1-methyl-1,2,3,4-tetrahydroquinolin-7-yl)ethyl)piperidin-4-one were dissolved in 4 ml of acetic acid. Thereafter, 0.49 g of sodium sulfate was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, 0.12 g of sodium triacetoxyborohydride was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, 4 ml of water was further added to the reaction solution, and the obtained mixture was then stirred at 100° C. for 2 hours. The reaction solution was cooled to a room temperature, followed by concentration under a reduced pressure. A saturated sodium bicarbonate aqueous solution was added to the residue, followed by extraction with chloroform. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol) and by NH silica gel column chromatography (ethyl acetate), so as to obtain 70 mg of the subject compound.

Workup

  1. stirringthe obtained mixture was then stirred at room temperature for 1 hour
  2. stirringthe obtained mixture was then stirred at 100° C. for 2 hours
  3. temperatureThe reaction solution was cooled to a room temperature
  4. concentrationfollowed by concentration under a reduced pressure
  5. additionA saturated sodium bicarbonate aqueous solution was added to the residue
  6. extractionfollowed by extraction with chloroform
  7. dry with materialThe extract was dried over magnesium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate-methanol) and by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-db7355154e8e4019bb99aeb609bc4e96
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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