Water → (3-Benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine Hemigalactarate

HRID 2305745Notes

Reaction equation

HRID 2305745 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][NH:14][CH3:15])=[CH:9][C:4]=2[O:3][CH2:2]1.[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].O>C(O)C>[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][NH:14][CH3:15])=[CH:9][C:4]=2[O:3][CH2:2]1.[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][NH:14][CH3:15])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 28260067(3-Benzo[34-d]1,3-dioxolan-5-yloxypropyl)methylamine

Product 1

HCID 131723466(3-Benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine Hemigalactarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3-benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine (0.252 g, 1.21 mmol) in ethanol (6 mL) was added galactaric acid (140.0 mg, 0.67 mmol). Water (1.5 mL) was added drop-wise, while warming the solution to near reflux. To remove some white, insoluble crystals, the warm solution was filtered through a glass wool plug, washing the filter plug with a warm solution of ethanol-water (4:1, v/v) (1.5 mL). The filtrate was diluted with ethanol (7.5 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 48 h. The precipitate was filtered, washed with ether, and vacuum dried at 40° C. for 16 h to give 301 mg (79.4%) of a white, crystalline solid, mp 158-160° C. The compound exhibits a Ki of 16600 nM. The compound exhibits neurotransmitter release of 41 percent.

Workup

  1. temperaturewhile warming the solution
  2. temperatureto near reflux
  3. customTo remove some white, insoluble crystals
  4. filtrationthe warm solution was filtered through a glass wool plug
  5. washwashing the filter plug with a warm solution of ethanol-water (4:1, v/v) (1.5 mL)
  6. additionThe filtrate was diluted with ethanol (7.5 mL)
  7. temperaturewas further cooled at 5° C. for 48 h
  8. filtrationThe precipitate was filtered
  9. washwashed with ether, and vacuum
  10. customdried at 40° C. for 16 h
  11. customto give 301 mg (79.4%) of a white, crystalline solid, mp 158-160° C

Sources & evidence

ORD record
ord-b3095186ec2848e3a9ee77b4ff0a1d78
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

Loading…