Formaldehyde → HCID 68777672, compound

HRID 1876813Notes

Reaction equation

HRID 1876813 reaction equation
C=O.[BH3-][C:4]#[N:5].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16]([N:18]2[CH:27]3[CH:22]([CH2:23][CH2:24][CH2:25][CH:26]3[N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)N[CH2:20][CH2:19]2)=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14].C([O-])([O-])=O.[Na+].[Na+]>CO.C(O)(=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16]([N:18]2[CH:27]3[CH:22]([CH2:23][CH2:24][CH2:25][CH:26]3[N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[N:5]([CH3:4])[CH2:20][CH2:19]2)=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 687760732-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one

Product 1

HCID 68777672HCID 68777672, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

Formalin (37%, 223 mg, 2.7 mmol) was dissolved in 5 ml of MeOH and NaBH3CN (17.2 mg, 0.27 mmol) was added. The pH was adjusted to 5 with concentrated acetic acid. 2-(3,4-Dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one (109 mg, 0.27 mmol), dissolved in MeOH (15 ml), was then added to the mixture and the mixture was stirred for 1.5 hours. After addition of saturated Na2CO3 solution (12 ml), the mixture was stirred at room temperature for 15 minutes. The precipitate formed was filtered off and MeOH was evaporated off from the filtrate under 100 mbar. The aqueous phase was extracted by shaking five times with CH2Cl2 and the combined organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 9.5:0.5:0.05, l=16 cm, V=5 ml). A yellowish resin was isolated.

Workup

  1. additionwas then added to the mixture
  2. stirringthe mixture was stirred at room temperature for 15 minutes
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. customMeOH was evaporated off from the filtrate under 100 mbar
  6. extractionThe aqueous phase was extracted
  7. stirringby shaking five times with CH2Cl2
  8. dry with materialthe combined organic phases were dried over Na2SO4
  9. customevaporated in vacuo
  10. customThe residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 9.5:0.5:0.05, l=16 cm, V=5 ml)
  11. customA yellowish resin was isolated

Sources & evidence

ORD record
ord-5bc3161f932b41e79b0d84f9fe0fed60
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Reaction notes

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