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

HRID 1828914Notes

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 L), 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 power, 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 power, mp 148–150° C.

Sources & evidence

ORD record: ord-deebc667031544b0869f6da6f9dfd153
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060826B2

Reaction notes

Loading…