Water → HCID 131722239, compound

HRID 2305578Notes

Reaction equation

HRID 2305578 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH3:13])[CH:5]=[N:6][CH:7]=1.[O:14]=[C:15]([OH:27])[C@@H:16]([C@H:18]([C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21])[OH:19])[OH:17].O>C(O)C>[O:14]=[C:15]([OH:27])[C@@H:16]([C@H:18]([C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21])[OH:19])[OH:17].[Br:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH3:13])[CH:5]=[N:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH3:13])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10198746HCID 10198746, compound

Product 1

HCID 131722239HCID 131722239, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3-(5-bromo(3-pyridyloxy))propyl)methylamine (0.790 g, 3.22 mmol) in ethanol (12 mL) was added galactaric acid (339.0 mg, 1.61 mmol). Water (3.4 mL) was added dropwise, while warming the light-yellow 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) (3.8 mL). The filtrate was diluted with ethanol (18 mL), producing a light-beige precipitate. 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 ethanol (5 mL), vacuum dried at 40 C. for 24 h to give 983.3 mg (68.8%) of a glassy, beige powder, mp 166-173.5° C. 1H NMR (D2O, 300 MHz): δ8.25 (d, 1H, J=1.78 Hz), 8.20 (d, 1H, J=2.54 Hz), 7.67 (dd, 1H, J=1.81, 1.81 Hz), 4.28 (s, 1H), 4.22 (t, 2H, J=5.70 Hz), 3.98 (s, 1H), 3.29 (t, 2H, J=7.21 Hz 2.79 (s, 3H), 2.25 (p, 2H, J=6.60 Hz). 13C NMR (D2O, 75 MHz): δ188.14, 182.32, 157.90, 145.18, 138.61, 128.05, 123.26, 74.58, 74.28, 69.05, 49.67, 35.86, 28.08. EI-MS: m/z (relative intensity) 246 (M+, 1.55%), 244 (M+, 1.54%), 175 (4.98%), 173 (5.10%), 118 (2.59%), 116 (2.66%), 70 (5.67%), 44 (100.00%), (9.89%). ES-MS: m/z 247, 245 [M+H]+.

Workup

  1. temperaturewhile warming the light-yellow 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) (3.8 mL)
  6. additionThe filtrate was diluted with ethanol (18 mL)
  7. customproducing a light-beige precipitate
  8. temperaturewas further cooled at 5° C. for 48 h
  9. filtrationThe precipitate was filtered
  10. washwashed with ethanol (5 mL), vacuum
  11. customdried at 40 C
  12. customfor 24 h to give 983.3 mg (68.8%) of a glassy, beige powder, mp 166-173.5° C

Sources & evidence

ORD record
ord-f53e8bcae6ad47e68533be2326ac3a8b
Source dataset
uspto-grants-2002_08
Patent number
US06441007B1

Reaction notes

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