3-(1-Methylpyrrolidin-2-yl)pyridine → Nicotine beta-cyclodextrin

HRID 2379383Notes

Reaction equation

HRID 2379383 reaction equation
[CH2:1]([OH:77])[C@H:2]1[O:7][C@@H:6]2[O:8][C@H:9]3[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@@H:12]([O:17][C@H:18]4[C@H:23]([OH:24])[C@@H:22]([OH:25])[C@@H:21]([O:26][C@H:27]5[C@H:32]([OH:33])[C@@H:31]([OH:34])[C@@H:30]([O:35][C@H:36]6[C@H:41]([OH:42])[C@@H:40]([OH:43])[C@@H:39]([O:44][C@H:45]7[C@H:50]([OH:51])[C@@H:49]([OH:52])[C@@H:48]([O:53][C@H:54]8[C@H:60]([OH:61])[C@@H:59]([OH:62])[C@@H:57]([O:58][C@H:3]1[C@H:4]([OH:76])[C@H:5]2[OH:75])[O:56][C@@H:55]8[CH2:63][OH:64])[O:47][C@@H:46]7[CH2:65][OH:66])[O:38][C@@H:37]6[CH2:67][OH:68])[O:29][C@@H:28]5[CH2:69][OH:70])[O:20][C@@H:19]4[CH2:71][OH:72])[O:11][C@@H:10]3[CH2:73][OH:74].[N:78]1[CH:83]=[C:82]([CH:84]2[CH2:89][CH2:88][CH2:87][N:85]2[CH3:86])[CH:81]=[CH:80][CH:79]=1>O>[N:78]1[CH:83]=[C:82]([CH:84]2[CH2:89][CH2:88][CH2:87][N:85]2[CH3:86])[CH:81]=[CH:80][CH:79]=1.[CH2:67]([OH:68])[C@H:37]1[O:38][C@@H:39]2[O:44][C@H:45]3[C@H:50]([OH:51])[C@@H:49]([OH:52])[C@@H:48]([O:53][C@H:54]4[C@H:60]([OH:61])[C@@H:59]([OH:62])[C@@H:57]([O:58][C@H:3]5[C@H:4]([OH:76])[C@@H:5]([OH:75])[C@@H:6]([O:8][C@H:9]6[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@@H:12]([O:17][C@H:18]7[C@H:23]([OH:24])[C@@H:22]([OH:25])[C@@H:21]([O:26][C@H:27]8[C@H:32]([OH:33])[C@@H:31]([OH:34])[C@@H:30]([O:35][C@H:36]1[C@H:41]([OH:42])[C@H:40]2[OH:43])[O:29][C@@H:28]8[CH2:69][OH:70])[O:20][C@@H:19]7[CH2:71][OH:72])[O:11][C@@H:10]6[CH2:73][OH:74])[O:7][C@@H:2]5[CH2:1][OH:77])[O:56][C@@H:55]4[CH2:63][OH:64])[O:47][C@@H:46]3[CH2:65][OH:66]

Participants

4

Reactant 2

HCID 9423-(1-Methylpyrrolidin-2-yl)pyridine2×HCID 444041beta-Cyclodextrin

Product 1

HCID 131718770Nicotine beta-cyclodextrin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An initial quantity of 56.76 g of β-cyclodextrin was placed in a 400 mL beaker and 5.68 g of H2O (equivalent to 10% of the powder) was added with stirring. The water was added in amounts of 1.9 g at a time, with stirring for 10 minutes at each step. The powder, before addition of nicotine, was similar to a wet granulate. Next, 6.37 g of nicotine was added very slowly with stirring, and at the end of the process the granulate was stirred for 10 minutes. The obtained granulate was dried in an oven at 35° C. for 2 hours. A sample was then analyzed for nicotine content.

Workup

  1. additionwas added
  2. stirringwith stirring for 10 minutes at each step
  3. stirringwith stirring
  4. stirringat the end of the process the granulate was stirred for 10 minutes
  5. customThe obtained granulate was dried in an oven at 35° C. for 2 hours

Sources & evidence

ORD record
ord-a7063e317feb403dba9cf2b52755c640
Source dataset
uspto-grants-1994_11
Patent number
US05362496

Reaction notes

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