1,2-Dichloroethane → N-Coumaroyl serotonin

HRID 1398723Notes

Reaction equation

HRID 1398723 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.Cl.[OH:14][C:15]1[CH:26]=[C:25]2[C:18]([NH:19][CH:20]=[C:21]2[CH2:22][CH2:23][NH2:24])=[CH:17][CH:16]=1.C(Cl)CCl.C(OCC)(=O)C>CCCCCC>[OH:14][C:15]1[CH:26]=[C:25]2[C:18](=[CH:17][CH:16]=1)[NH:19][CH:20]=[C:21]2[CH2:22][CH2:23][NH:24][C:8](=[O:10])/[CH:7]=[CH:6]/[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 3224-Coumaric acidHCID 8857Ethyl AcetateHCID 160436Serotonin Hydrochloride

Product 1

HCID 5458879N-Coumaroyl serotonin

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

(E)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide (2b) was synthesized according to by the condensation of 4-hydroxy cinnamic acid (150 mg, 0.914 mmol) and 5-hydroxy tryptamine hydrochloride (232 mg, 1.09 mmol) using standard EDC coupling method. 2b was isolated as reddish semi solid (182 mg 62%) by elution with 55% ethyl acetate in hexane. Rf: 0.58 (ethyl acetate);

Workup

  1. custom(E)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide (2b) was synthesized

Sources & evidence

ORD record
ord-cf67d0f9f5cb49c8a598038d401cb48d
Source dataset
uspto-grants-2014_12
Patent number
US08901317B2

Reaction notes

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