1,2-Dichloroethane → 3,4,5-tris(benzyloxy)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzamide

HRID 1398722Notes

Reaction equation

HRID 1398722 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH:35][C:36]1[CH:47]=[C:46]2[C:39]([NH:40][CH:41]=[C:42]2[CH2:43][CH2:44][NH2:45])=[CH:38][CH:37]=1.C(Cl)CCl.CO>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17]=1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:12]([NH:45][CH2:44][CH2:43][C:42]1[C:46]2[C:39](=[CH:38][CH:37]=[C:36]([OH:35])[CH:47]=2)[NH:40][CH:41]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 887MethanolHCID 160436Serotonin HydrochlorideHCID 111339693,4,5-Tris(benzyloxy)benzoic Acid

Product 1

HCID 668037303,4,5-tris(benzyloxy)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2a was synthesized by the condensation of 3,4,5-tris(benzyloxy)benzoic acid (860 mg, 1.95 mmol) and 5-hydroxy tryptamine hydrochloride (496 mg, 2.34 mmol) according using standard EDC coupling method. The compound was isolated as white solid (874 mg, 75%) by elution with 2% methanol in chloroform. Rf: 0.470 (5% methanol in chloroform).

Sources & evidence

ORD record
ord-169cd1b1db5148dd9541f1c282a88224
Source dataset
uspto-grants-2014_12
Patent number
US08901317B2

Reaction notes

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