Water → (3-(5-Chloro(3-pyridyloxy))-1-methylpropyl)methylamine Hemigalactarate

HRID 2305732Notes

Reaction equation

HRID 2305732 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH:11]([NH:13][CH3:14])[CH3:12])[CH:5]=[N:6][CH:7]=1.[O:15]=[C:16]([OH:28])[C@@H:17]([C@H:19]([C@H:21]([C@@H:23]([C:25]([OH:27])=[O:26])[OH:24])[OH:22])[OH:20])[OH:18].O>C(O)C>[O:15]=[C:16]([OH:28])[C@@H:17]([C@H:19]([C@H:21]([C@@H:23]([C:25]([OH:27])=[O:26])[OH:24])[OH:22])[OH:20])[OH:18].[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH:11]([NH:13][CH3:14])[CH3:12])[CH:5]=[N:6][CH:7]=1.[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH:11]([NH:13][CH3:14])[CH3:12])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9942566(3-(5-Chloro(3-pyridyloxy))-1-methylpropyl)methylamine

Product 1

HCID 131723464(3-(5-Chloro(3-pyridyloxy))-1-methylpropyl)methylamine Hemigalactarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3-(5-chloro(3-pyridyloxy))-1-methylpropyl)-methylamine (0.70 g, 3.27 mmol) in ethanol (20 mL) at 70° C. was added galactaric acid (0.343 g, 1.63 mmol). Water (0.5 mL) was added drop-wise while stirring, producing a clear solution. Some white, insoluble solids were removed by filtration. The filtrate was concentrated to 10 mL and was allowed to cool to ambient temperature. After standing 16 h, the precipitate was filtered, washed with ether (10 mL) and vacuum dried at 45° C. for 24 h to give 0.775 g (74.3%) of a light-beige, amorphous powder, mp 155-157° C. The compound exhibits a Ki of 1601 nM. The compound exhibits neurotransmitter release of 30 percent.

Workup

  1. customproducing a clear solution
  2. customSome white, insoluble solids were removed by filtration
  3. concentrationThe filtrate was concentrated to 10 mL
  4. filtrationthe precipitate was filtered
  5. washwashed with ether (10 mL) and vacuum
  6. customdried at 45° C. for 24 h
  7. customto give 0.775 g (74.3%) of a light-beige, amorphous powder, mp 155-157° C

Sources & evidence

ORD record
ord-51c8253ab0ba46439686a3b658ddf8e6
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

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