Water → (4E)-N-Methyl-5-(3-pyridyl)-4-penten-2-amine Hemigalactarate

HRID 489742

Reaction equation

[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:4].[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].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:4].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

(4E)-N-Methyl-5-(3-pyridyl)-4-penten-2-amine (1.60 g, 9.10 mmol) was dissolved in ethyl alcohol (20 mL), assisted by warming to 60° C. The warm solution was treated with galactaric acid (955 mg, 4.54 mmol) in one portion, followed by the dropwise addition of water (0.5 mL). The solution was filtered while hot to remove some insoluble material. The filtrate was allowed to cool to ambient temperature. The resulting crystals were filtered, washed with anhydrous diethyl ether, and dried under vacuum at 40° C. to yield 1.20 g (47.0%) of a white, crystalline powder, mp 148-150° C.

Workup

filtrationThe solution was filtered while hot
customto remove some insoluble material
temperatureto cool to ambient temperature
filtrationThe resulting crystals were filtered
washwashed with anhydrous diethyl ether
customdried under vacuum at 40° C.
customto yield 1.20 g (47.0%) of a white, crystalline powder, mp 148-150° C.

Sources & evidence

ORD record: ord-0bf00be2289647b3af150868dc494e11
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979695B2

Linked notes

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