Potassium Carbonate → HCID 22823462, compound

HRID 2166739Notes

Reaction equation

HRID 2166739 reaction equation
[OH:1][C:2]1[C:15]2[C@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:28]1[N:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:31]=[N:30][N:29]=1>CN(C=O)C>[CH3:19][N:18]1[CH2:17][CH2:16][C@@:14]23[C:15]4[C:2]([O:1][C:28]5[N:32]([C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=6)[N:31]=[N:30][N:29]=5)=[CH:3][CH:4]=[CH:5][C:6]=4[CH2:7][C@@H:8]1[C@@H:9]2[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 21603245HCID 21603245, compound

Product 1

HCID 22823462HCID 22823462, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.57 g (5.79 mmol) 4-hydroxy-N-methylmorphinan-6-one, 1.57 g (11.36 mmol) dry K2CO3 and 1.15 g (6.37 mml) 5-chloro-1-phenyl-1H-tetrazole din 30 ml dry DMF was stirred under argon for 24 h at room temperature. Then the reaction mixture was filtered, washed with CHCl3 and the filtrate was evaporated in vacuo (70° bath temperature). The oily residue was dissolved in CHCl3 and extracted with 2×20 ml 5% tartaric acid. The aqueous layer was rendered alkaline with conc. NaOH and extracted with CHcl3. The organic layer was washed with brine, dried and evaporated to give 2.2 g of an oil, which was crystallized with EtOAc/Et2O to yield 2.05 g (85%) of N-methyl-4-(1-phenyl-1H-5-tetrazolyloxy) morphinen-6-one, m.p. 172°-174°, [α]D26 -37.4° (c 1.35, CHCl3).

Workup

  1. filtrationThen the reaction mixture was filtered
  2. washwashed with CHCl3
  3. customthe filtrate was evaporated in vacuo (70° bath temperature)
  4. dissolutionThe oily residue was dissolved in CHCl3
  5. extractionextracted with 2×20 ml 5% tartaric acid
  6. extractionextracted with CHcl3
  7. washThe organic layer was washed with brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-b567637d63c14d2bb5d28dff14fa549c
Source dataset
uspto-grants-1983_06
Patent number
US04388463

Reaction notes

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