HCID 131714981, compound → HCID 20203559, compound

HRID 1732067Notes

Reaction equation

HRID 1732067 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][CH2:14][C:15](=[N:16]O)[C:7]1=[C:6]2[CH3:18]>C(O)C.[OH-].[Na+].[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][CH2:14][CH:15]([NH2:16])[C:7]1=[C:6]2[CH3:18]

Participants

5

Reactant 1

HCID 131714981HCID 131714981, compound

Product 1

HCID 20203559HCID 20203559, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

Raney alloy (10.2 g) was added portionwise (over 40 minutes) to a solution of 6,7,8,9-tetrahydro-2-methoxy-10-methylpyrido[1,2-a]indol-9-one oxime (6.2 g, 25.4 mmol) in ethanol (200 mL) and 10% aqueous sodium hydroxide (100 mL) at ~35° C. The reaction mixture was stirred at 40° C. for 12 hours, cooled to 25° C., and then poured into icy, saturated brine solution (500 mL). The product was extracted with ether (2×200 mL), and the combined extracts were washed with 5% hydrochloric acid (200 mL). Upon cooling the separated aqueous layer was rendered basic with 50% aqueous sodium hydroxide, and extracted with ether (3×150 mL). The ethereal extracts were dried over MgSO4, filtered, and evaporated to afford 5.8 g (99%) of the title amine as a yellow oil.

Workup

  1. temperaturecooled to 25° C.
  2. extractionThe product was extracted with ether (2×200 mL)
  3. washthe combined extracts were washed with 5% hydrochloric acid (200 mL)
  4. temperatureUpon cooling the separated aqueous layer
  5. extractionextracted with ether (3×150 mL)
  6. dry with materialThe ethereal extracts were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e4ac7acd575e4ea1a977caf80276b3d7
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

Loading…