Ammonia → Bupivacaine (USAN:INN:BAN)

HRID 1957724Notes

Reaction equation

HRID 1957724 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C@H:10]([C:11]([NH:13][C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:21])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1.C(O)(=O)CC.O.N>C(OCC)(=O)C>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:10]([C:11]([NH:13][C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:21])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 1032Propionic AcidHCID 92253Levobupivacaine

Product 1

HCID 2474Bupivacaine (USAN:INN:BAN)Yield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of (S)-bupivacaine (0.140 g, 0.49 mmol) and propanoic acid (3.5 ml) was heated to reflux under a nitrogen atmosphere for 7 hours. The resulting solution was cooled and then poured into a mixture of distilled water (20 ml) and ethyl acetate (20 ml). Aqueous ammonia (28% w/v) was added until the pH of the aqueous layer was 10. The organic layer was separated and the aqueous layer extracted with ethyl acetate (20 ml). The combined organic extracts were washed with distilled water (20 ml), dried (MgSO4) and concentrated under reduced pressure to give racemic bupivacaine (0.137 g, 98%). ##STR1##

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a nitrogen atmosphere for 7 hours
  3. temperatureThe resulting solution was cooled
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with ethyl acetate (20 ml)
  6. washThe combined organic extracts were washed with distilled water (20 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81cba8b0624a4fcaa3661b11a6e13137
Source dataset
uspto-grants-1998_07
Patent number
US05786484

Reaction notes

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