Fumaric Acid → HCID 67751258, compound

HRID 248841Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:10])[CH3:9])[C@H:4]([O:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH3:15])[CH2:3]1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>O1CCCC1.C(O)(C)C>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:9])[CH3:10])[C@H:4]([O:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH3:15])[CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

4.27 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-[2-(3,4-dimethoxybenzyloxy)ethyl]-N-methylamine base were dissolved in 50 ml of tetrahydrofuran. A solution of 1.22 g of fumaric acid in 15 ml of isopropanol was added to the solution. The solution was concentrated to a volume of about 20 ml under reduced pressure, and a mixture of diethyl ether/n-hexane was added until the solution became cloudy, after which the solution was cooled to 0° C. The precipitated crystals were filtered out and dried at 50° C. 4.28 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)et hyl]-N-[2-(3,4-dimethoxybenzyloxy)ethyl]-N-methylamine fumarate having a melting point of 72° C.-73° C. were obtained. [α]D20 =-37.0° (c=1; methanol)

Workup

concentrationThe solution was concentrated to a volume of about 20 ml under reduced pressure
additiona mixture of diethyl ether/n-hexane
additionwas added until the solution
filtrationThe precipitated crystals were filtered out
customdried at 50° C

Sources & evidence

ORD record: ord-066fc7b4dd914816bff6bb8eadfbf488
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05212173

Reaction notes

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