Triethylamine → Nalbuphine propionate

HRID 1975972Notes

Reaction equation

HRID 1975972 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+]>ClCCl>[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 6344DichloromethaneSolvent2×

Procedure

75 ml of methylene chloride and 3.57 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 stirred then gradually 0.16 mole of triethylamine was added. With rapid stirring, another 20 ml of dichloromethane solution containing 0.011 mole of 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.

Workup

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

Sources & evidence

ORD record
ord-8fe1c654bc8748699411052a55d86e20
Source dataset
uspto-grants-2001_05
Patent number
US06225321B1

Reaction notes

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