Diethyl Ether → HCID 86755879, compound

HRID 365405Notes

Reaction equation

HRID 365405 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1.[CH2:26]([O:28]CC)[CH3:27]>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 86755876HCID 86755876, compound

Product 1

HCID 86755879HCID 86755879, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

1.0 g of (+/-)-cis-8,9-dimethoxy-6-(4-aminophenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine is suspended in 10 ml of acetic anhydride and the suspension is stirred at RT for 1 h. The solution is treated with diethyl ether, and the precipitate is filtered off with suction and extracted with sodium hydrogencarbonate solution/ethyl acetate. After drying and concentration of the organic phase, the residue is recrystallized from ethyl acetate/methanol. 0.63 g (56.0% of theory) of the title compound of m.p. 218° C. is obtained.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. extractionextracted with sodium hydrogencarbonate solution/ethyl acetate
  3. customAfter drying
  4. customconcentration of the organic phase, the residue is recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-9d01df109f4d43b4980064a66cafd612
Source dataset
uspto-grants-2000_10
Patent number
US06127378

Reaction notes

Loading…