Cyanuric chloride → HCID 16638913, compound

HRID 1374538Notes

Reaction equation

HRID 1374538 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1.[CH3:10][O:11][C:12]1[CH:29]=[CH:28][C:15]2[CH2:16][NH:17][CH2:18][CH2:19][C@@:20]34[C@@H:25]([O:26][C:13]=1[C:14]=23)[CH2:24][C@@H:23]([OH:27])[CH:22]=[CH:21]4.[OH-].[Na+]>CC(C)=O>[Cl:9][C:4]1[N:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:17]2[CH2:18][CH2:19][C:20]34[CH:21]=[CH:22][C@H:23]([OH:27])[CH2:24][CH:25]3[O:26][C:13]3=[C:12]([O:11][CH3:10])[CH:29]=[CH:28][C:15](=[C:14]43)[CH2:16]2)[N:3]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 9838394N-Desmethylgalanthamine

Product 1

HCID 16638913HCID 16638913, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2,4,6-trichloro-1,3,5-triazine (0.66 g, 3.7 mmol) in acetone (16 ml) was poured onto ice water (35 ml) and added in small portions at 0° C. to (+/−)-norgalanthamine (1.0 g, 3.7 mmol). After the addition of 2N-sodium hydroxide (2 ml), the reaction mixture was refluxed for 40 hours. The aqueous phase was extracted with EtOAc (3×30 ml). The combined, organic phases were washed with common salt solution (30 ml), dried (Na2SO4) and concentrated by evaporation, to produce 0.90 g (59.5%) of compound 4e: 1H-NMR (CDCl3) δ 6.82 (d, J=10.0 Hz, 1H), 6.63 (d, J=10.0 Hz, 1H), 6.02 (b, 2H), 5.30 (d, J=11.0 Hz, 1H), 4.75 (d, J=16.0, 1H), 4.50 (b, 1H), 4.22 (d, J=11.0 Hz, 1H), 4.11 (b, 1H), 3.78 (s, 3H), 3.59 (m, 1H), 3.06 (m, 1H), 2.61 (d, J=16.0 Hz, 1H), 1.90 (m, 3H); 13C-NMR (CDCl3) δ 207.0 (s) 171.2 (s), 163.7 (s), 146.2 (s), 143.9 (s), 132.3 (d), 129.5 (s), 127.6 (s), 126.7 (d), 121.5 (d), 110.8 (d), 88.0 (d), 61.7 (d), 55.7 (q), 51.8 (t), 48.2 (5), 43.4 (t), 35.9 (t), 29.7 (t).

Workup

  1. temperaturethe reaction mixture was refluxed for 40 hours
  2. extractionThe aqueous phase was extracted with EtOAc (3×30 ml)
  3. washorganic phases were washed with common salt solution (30 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-824db1f010904b579826f754dec3b8d8
Source dataset
uspto-grants-2007_01
Patent number
US07166588B2

Reaction notes

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