Water → Traboxopine

HRID 1164783Notes

Reaction equation

HRID 1164783 reaction equation
C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[Cl:11][C:12]1[CH:34]=[CH:33][C:15]2[O:16][CH2:17][O:18][C:19]3[CH:32]=[CH:31][CH:30]=[CH:29][C:20]=3[N:21]([CH2:22][CH:23]([CH3:28])[CH2:24][N:25]([CH3:27])[CH3:26])[C:14]=2[CH:13]=1.O>ClCCl>[Cl:11][C:12]1[CH:34]=[CH:33][C:15]2[O:16][CH2:17][O:18][C:19]3[CH:32]=[CH:31][CH:30]=[CH:29][C:20]=3[N:21]([CH2:22][CH:23]([CH3:28])[CH2:24][N:25]([CH3:27])[CH3:26])[C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 962WaterHCID 14555943HCID 14555943, compound

Product 1

HCID 129812TraboxopineYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 19.0 g (0.038 moles) of (-)-2-chloro-12-(3-dimethylamino-2-methylpropyl)-12H-dibenzo[d,g][1,3,6]dioxazocine L(+)-tartrate, 100 cm3 of water and 100 cm3 of dichloromethane 25 percent aqueous ammonia is added until a pH value of 10. The mixture is stirred for further 30 minutes, the organic phase is separated and the solvent is removed under reduced pressure. The viscous residue is dissolved in 28 cm3 of isopropanol, cooled to 0° C. and the crystals are filtered. 11.1 g 84.0% of the title compound are obtained, m.p.: 92°-95° C.

Workup

  1. additionis added until a pH value of 10
  2. customthe organic phase is separated
  3. customthe solvent is removed under reduced pressure
  4. dissolutionThe viscous residue is dissolved in 28 cm3 of isopropanol
  5. filtrationthe crystals are filtered

Sources & evidence

ORD record
ord-62a4da17b0f84c29917788d7ef6e96d0
Source dataset
uspto-grants-1990_03
Patent number
US04906622

Reaction notes

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