Sodium Hydroxide → HCID 68777946, compound

HRID 1876804Notes

Reaction equation

HRID 1876804 reaction equation
[CH2:1]([N:8]1[CH:17]2[CH:12]([CH:13]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:15][CH2:16]2)[NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH2:31][C:32](Cl)=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30].[OH-].[Na+]>C(Cl)Cl>[CH2:1]([N:8]1[CH:17]2[CH:12]([CH:13]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:15][CH2:16]2)[N:11]([C:32](=[O:33])[CH2:31][C:26]2[CH:27]=[CH:28][C:29]([Cl:30])=[C:24]([Cl:23])[CH:25]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27581492-(3,4-Dichlorophenyl)acetyl chlorideHCID 68778430HCID 68778430, compound

Product 1

HCID 68777946HCID 68777946, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4aRS,5SR,8aRS)-1-Benzyl-5-(pyrrolidin-1-yl)perhydroquinoxaline (325 mg, 1.09 mmol) was dissolved in absolute CH2Cl2 (35 ml). 2-(3,4-Dichlorophenyl)acetyl chloride (291 mg, 1.3 mmol) was added dropwise and the mixture was stirred at room temperature. After 30 minutes, 2 N NaOH (35 ml) was added and the mixture was stirred vigorously for 2 hours. The aqueous phase was separated off. The organic phase was extracted by shaking three times with HCl (1 N). The aqueous phase was then brought to pH 8 with NaOH (2 N) and extracted by shaking three times with CH2Cl2. The organic phases were dried over Na2SO4 and evaporated in vacuo. The product was obtained as a pale yellow solid.

Workup

  1. stirringthe mixture was stirred vigorously for 2 hours
  2. customThe aqueous phase was separated off
  3. extractionThe organic phase was extracted
  4. stirringby shaking three times with HCl (1 N)
  5. extractionextracted
  6. stirringby shaking three times with CH2Cl2
  7. dry with materialThe organic phases were dried over Na2SO4
  8. customevaporated in vacuo
  9. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-f370c147b9b7482db93357a74f039990
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Reaction notes

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