Pilocarpine → Pilocarpine Alpha Tocopherol Hemisuccinate

HRID 2254018

Reaction equation

HRID 2254018 reaction equation
[CH3:1][CH2:2][C@@H:3]1[C:7](=[O:8])[O:6][CH2:5][C@@H:4]1[CH2:9][C:10]1[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=1.[CH3:16][C:17]1[C:22]([CH3:23])=[C:21]([O:24][C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])[C:20]([CH3:32])=[C:19]2[CH2:33][CH2:34][C@:35]([CH2:38][CH2:39][CH2:40][C@@H:41]([CH2:43][CH2:44][CH2:45][C@@H:46]([CH2:48][CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[CH3:47])[CH3:42])([CH3:37])[O:36][C:18]=12.CC1C(C)=C2C(CC[C@](CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)(C)O2)=C(C)C=1O>C(Cl)Cl>[CH3:1][CH2:2][C@@H:3]1[C:7](=[O:8])[O:6][CH2:5][C@@H:4]1[CH2:9][C:10]1[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=1.[CH3:16][C:17]1[C:22]([CH3:23])=[C:21]([O:24][C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])[C:20]([CH3:32])=[C:19]2[CH2:33][CH2:34][C@:35]([CH2:38][CH2:39][CH2:40][C@@H:41]([CH2:43][CH2:44][CH2:45][C@@H:46]([CH2:48][CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[CH3:47])[CH3:42])([CH3:37])[O:36][C:18]=12

Participants

5

Reactant 3

HCID 5910Pilocarpine2×HCID 14985alpha-TocopherolHCID 20353alpha-Tocopherol succinate

Product 1

HCID 131716046Pilocarpine Alpha Tocopherol Hemisuccinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Five grams of pilocarpine base were added to a weighed 500 ml round bottom flask and stopper, and the total mass in grams recorded. D-alpha-tocopherol acid succinate (12.75 g, corresponding to a 1:1 M ratio of pilocarpine:D-alpha-tocopherol) was added to the flask and the contents again weighed. Methylene chloride (50 ml) was added and the flask agitated to dissolve the solids and the flask again weighed. The flask was placed on a rotary evaporator in a water bath at 55° C. and rotated for 30 minutes (no vacuum applied). After 30 minutes, the flask and contents were again weighed, then rotary evaporated with vacuum at 55° C. The weight of the flask was recorded every 30 minutes thereafter until two successive weighings were within 0.1 g. The preparation was then cooled to room temperature (25° C.), stoppered, and stored at 4° C.

Workup

  1. dissolutionto dissolve the solids
  2. customThe flask was placed on a rotary evaporator in a water bath at 55° C.
  3. waitAfter 30 minutes
  4. customrotary evaporated with vacuum at 55° C
  5. waitThe weight of the flask was recorded every 30 minutes
  6. customstored at 4° C.

Sources & evidence

ORD record
ord-9214be1220194a9092220208fec72f40
Source dataset
uspto-grants-1993_08
Patent number
US05234634

Linked notes

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