Sodium Hydroxide → HCID 50992301, compound

HRID 1405493Notes

Reaction equation

HRID 1405493 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[C:22]([N:23]4[CH2:28][CH2:27][CH:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:25][CH2:24]4)=[N:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:35]([O:37]CC)=[O:36])[CH:19]=4)[N:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:13]3[C:22]([N:23]4[CH2:24][CH2:25][CH:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:27][CH2:28]4)=[N:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:35]([OH:37])=[O:36])[CH:19]=4)[N:14]=3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67041967HCID 67041967, compound

Product 1

HCID 50992301HCID 50992301, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of ethyl 2,3-bis(4-phenylpiperidin-1-yl)quinoxaline-6-carboxylate (150 mg, 0.29 mmol, 1.00 equiv) in methanol (25 mL) and a solution of sodium hydroxide (58 mg, 1.45 mmol, 5.00 equiv) in water (2 mL). The resulting solution was stirred for 3 h at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 30 mL of water. The pH value of the aqueous solution was adjusted to 3 with 1N hydrochloric acid. The resulting solids were collected by filtration. The solid was dried in an oven under reduced pressure and purified by re-crystallization from methanol. This resulted in 80 mg (56%) of 2,3-bis(4-phenylpiperidin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe resulting solution was diluted with 30 mL of water
  4. filtrationThe resulting solids were collected by filtration
  5. customThe solid was dried in an oven under reduced pressure
  6. custompurified by re-crystallization from methanol
  7. customThis resulted in 80 mg (56%) of 2,3-bis(4-phenylpiperidin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-7df9d3bc25c04cfda8e1d0f85b55925d
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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