Ammonium Chloride → HCID 131723314, compound

HRID 2187504Notes

Reaction equation

HRID 2187504 reaction equation
[CH2:1]([O:3][C:4]1[CH:17]=[C:16]2[C:7]([C:8]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)=[N:9][C@@H:10]3[C@H:15]2[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:6][C:5]=1[O:26][CH3:27])[CH3:2].[Cl-].[NH4+].[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:17]=[C:16]2[C:7]([C:8]([C:18]3[CH:19]=[CH:20][C:21]([C:24]4[N:30]=[N:31][NH:32][N:25]=4)=[CH:22][CH:23]=3)=[N:9][C@@H:10]3[C@H:15]2[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:6][C:5]=1[O:26][CH3:27])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 70089088HCID 70089088, compound2×

Product 1

HCID 131723314HCID 131723314, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.2 g of (+/−)-cis-9-ethoxy-8-methoxy-6-(4-cyano-phenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine (compound A1), 0.65 g of ammonium chloride and 0.83 g of sodium azide are suspended in 150 ml of abs. dimethylformamide and heated at 120° C. for 24 h. The reaction mixture is partitioned between water and diethyl ether, and the organic phase is dried with sodium sulfate and concentrated. The residue is chromatographed on silica gel using methylene chloride/methanol in the ratio 4/1. After concentration of the corresponding eluate fractions, the title compound is obtained as a solidified oil.

Workup

  1. customThe reaction mixture is partitioned between water and diethyl ether
  2. dry with materialthe organic phase is dried with sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-28572e8e03da43a4a367bac8ca0de933
Source dataset
uspto-grants-2002_06
Patent number
US06410551B1

Reaction notes

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