Triethylamine → Nalbuphine propionate

HRID 1289465Notes

Reaction equation

HRID 1289465 reaction equation
[CH:1]1[C:6]2[CH2:7][C@H:8]3[N:13]([CH2:14][CH:15]4[CH2:18][CH2:17][CH2:16]4)[CH2:12][CH2:11][C@:10]45[C@H:19]([C@@H:21]([OH:24])[CH2:22][CH2:23][C@@:9]34[OH:25])[O:20][C:4]([C:5]=25)=[C:3]([OH:26])[CH:2]=1.C(N(CC)CC)C.[C:34]([O:38]C(=O)CC)(=[O:37])[CH2:35][CH3:36].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH:1]1[C:6]2[CH2:7][C@H:8]3[N:13]([CH2:14][CH:15]4[CH2:18][CH2:17][CH2:16]4)[CH2:12][CH2:11][C@:10]45[C@H:19]([C@@H:21]([OH:24])[CH2:22][CH2:23][C@@:9]34[OH:25])[O:20][C:4]([C:5]=25)=[C:3]([OH:26])[CH:2]=1.[C:34]([O-:38])(=[O:37])[CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31263Propionic anhydrideHCID 5311304Nalbuphine

Product 1

HCID 86752538Nalbuphine propionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

75 mL of methylene chloride and 3.75 g (0.01 mole) of nalbuphine were added to a 250-mL round-bottomed flask. The flask was placed in an ice bath to keep it cool. The content was then stirred and then gradually a 20 mL of methylene chloride solution containing 0.16 mole of triethylamine was added. With rapid stirring, another 20 mL of methylene chloride solution containing 0.011 mole of dry propionic anhydride was added drop by drop. Afterward, the mixture was stirred at room temperature for 1 hour. 20 mL of 10% sodium carbonate solution was added to neutralize the residual acid and remove the water soluble impurities. Sodium sulfate was used to dehydrate the solution. After drying under vacuum, a nalbuphine propionate solid was obtained. The product was purified by column chromatography. The physical data are shown in Table 1 and FIGS. 4 and 5.

Workup

  1. customThe flask was placed in an ice bath
  2. temperaturecool
  3. additionwas added
  4. additionwas added drop by drop
  5. stirringAfterward, the mixture was stirred at room temperature for 1 hour
  6. customremove the water soluble impurities
  7. customAfter drying under vacuum

Sources & evidence

ORD record
ord-47a9ffa97d524da3bdeee8bda331265d
Source dataset
uspto-grants-1998_05
Patent number
US05750534

Reaction notes

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