Sodium Carbonate → HCID 86752369, compound

HRID 1598016Notes

Reaction equation

HRID 1598016 reaction equation
[CH:1]([C@@H:3]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:8][C@H:7]2[N:18]([CH3:19])[C@@H:4]1[CH2:5][CH2:6]2)=O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[OH:27][NH3+:28]>CO.C(O)C>[Cl:17][C:12]1[CH:11]=[C:10]([C@H:9]2[CH2:8][C@H:7]3[N:18]([CH3:19])[C@H:4]([CH2:5][CH2:6]3)[C@@H:3]2[CH:1]=[N:28][OH:27])[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21645Hydroxylamine HClHCID 86752368HCID 86752368, compound

Product 1

HCID 86752369HCID 86752369, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of (1R,2R,3S)-2-formyl-3-(3,4-dichlorophenyl)tropane (6.9 g, 23 mmol) in methanol (100 ml), sodium carbonate (4 g) and hydroxylammonium chloride (2.6 g, 37 mmol) were added, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was triturated with water. A crude product was isolated by filtration and recrystallization first in a mixture of ethanol and water (1+1) and then in 99% ethanol yielded the title compound (mixture of syn/anti isomers--approximately 1+2) as white crystals, m.p. 230°-235° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was triturated with water
  3. customA crude product was isolated by filtration and recrystallization first in a mixture of ethanol and water (1+1)

Sources & evidence

ORD record
ord-0d5f773f6ed14f8998e33d2cd7de966e
Source dataset
uspto-grants-1998_04
Patent number
US05736556

Reaction notes

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