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

HRID 494973Notes

Reaction equation

HRID 494973 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].[C:17]([N:20]1[C:29]2[C:24](=[CH:25][C:26]([O:39][CH3:40])=[C:27]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]3)[CH:28]=2)[CH2:23][CH2:22][CH2:21]1)(=[O:19])[CH3:18].S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.O>[C:17]([N:20]1[C:29]2[C:24](=[CH:25][C:26]([O:39][CH3:40])=[C:27]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH:35]([N:1]4[C:2]5[C:10](=[CH:9][CH:8]=[C:4]([C:5]([NH2:7])=[O:6])[CH:3]=5)[CH:11]=[CH:12]4)[CH2:34][CH2:33]3)[CH:28]=2)[CH2:23][CH2:22][CH2:21]1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 576827803-Amino-4-(2,2-dimethoxyethyl)benzamideHCID 576828631-(2-(1-Acetyl-6-methoxy-1,2,3,4-tetrahydroquinolin-7-yl)ethyl)piperidin-4-one

Product 1

HCID 576828751-{1-[2-(1-Acetyl-6-methoxy-1,2,3,4-tetrahydroquinolin-7-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxamideYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

172 mg of 3-amino-4-(2,2-dimethoxyethyl)benzamide and 127 mg of 1-(2-(1-acetyl-6-methoxy-1,2,3,4-tetrahydroquinolin-7-yl)ethyl)piperidin-4-one were dissolved in 5 ml of acetic acid. Thereafter, 0.65 g of sodium sulfate was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, 0.16 g of sodium triacetoxyborohydride was added to the reaction solution, and the obtained mixture was then stirred for 1 hour. Thereafter, 5 ml of water was added thereto, and the obtained mixture was then stirred at 100° C. for 2 hours. The reaction solution was cooled to a room temperature, and it was then concentrated 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 (chloroform-methanol) and NH silica gel column chromatography (ethyl acetate-methanol), so as to obtain 146 mg of the subject compound.

Workup

  1. stirringthe obtained mixture was then stirred 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. concentrationit was then concentrated 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 (chloroform-methanol) and NH silica gel column chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-1399423776ae469baaadabba6dfe8988
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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