Acetamide, N-(2-(5-methoxy-2-methyl-3-indolyl)ethyl)- → N-[2-(5-Methoxy-2-methyl-1H-indol-3-yl)ethyl]cyclopropanecarboxamide

HRID 741699Notes

Reaction equation

HRID 741699 reaction equation
[CH3:1][C:2]1[NH:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[C:3]=1[CH2:4][CH2:5][NH2:6].[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1.CC1NC2C=CC(OC)=CC=2C=1CCNC(C)=O>C1COCC1>[CH3:1][C:2]1[NH:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[C:3]=1[CH2:4][CH2:5][NH:6][C:19]([CH:16]1[CH2:18][CH2:17]1)=[O:20]

Participants

5

Reactant 3

HCID 50279Acetamide, N-(2-(5-methoxy-2-methyl-3-indolyl)ethyl)-HCID 528992-(5-Methoxy-2-methyl-1H-indol-3-yl)ethanamineHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 9970471N-[2-(5-Methoxy-2-methyl-1H-indol-3-yl)ethyl]cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the crude 2-methyl-5-methoxytryptamine (from 5 mmol of 3a), in THF (15 mL) and TEA (0.7 mL) was acylated with cyclopropanecarbonyl chloride (0.45 mL) at room temperature for 1.5 h using the procedure described for 4a. The desired product 4e was obtained as white solid (0.615 g, 45% overall yield), mp 102°-103° C. IR νmax : 3460, 3300, 1650. 1H NMR: 0.70(m, 2H, CH2cyclopropyl), 0.97(m, 2H, CH2 cyclopropyl), 1.24(m, 1H, cyclopropyl-CH), 2.36(s, 3H, 2-CH3), 2.90(t, 2H, β -CH2), 3.51(q, 2H, α-CH2), 3.85(s, 3H, OCH3), 5.75(br s, 1H, NH), 6.75-7.25 (m, 3Harom), 8.00(br s, 1H, NHindole).

Sources & evidence

ORD record
ord-8ee3aad904a04bfbb4e310837470a8eb
Source dataset
uspto-grants-1996_09
Patent number
US05552428

Reaction notes

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