N-[2-(5-methoxy-1H-indol-3-yl)ethyl]cyclopropanecarboxamide → HCID 10449713, compound

HRID 741700Notes

Reaction equation

HRID 741700 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([C:12]([NH:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[NH:19][CH:18]=2)=[O:13])[CH2:11][CH2:10]1.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:18]1[NH:19][C:20]2[C:25](=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:17]=1[CH2:16][CH2:15][NH:14][C:12]([CH:9]1[CH2:11][CH2:10]1)=[O:13]

Participants

5

Reactant 3

HCID 2877N-[2-(5-methoxy-1H-indol-3-yl)ethyl]cyclopropanecarboxamideHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide

Product 1

HCID 10449713HCID 10449713, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-bromo succinimide (0.89 g, 5 mmol) was added to a solution of N-cyclopropanoyl-5-methoxytryptamine, 4j (1.29 g, 5 mmol) in acetic acid (20 mL). The reaction mixture was stirred under N2 at room temperature for 4 h, then cooled at 0° C., neutralized with a 50% solution of NaOH and extracted with ethyl acetate. The combined organic layers were washed with NaCl solution, dried (Na2SO4) and concentrated. Purification by flash chromatography (silica gel; ethyl acetate/cyclohexane 6:4) and crystallization gave 0.490 g (29% yield) of 4h as white solid, mp 82°-83° C. IR νmax : 3460, 3300, 1650. 1H NMR: 0.72(m, 2H, CH2cyclopropyl), 0.99(m, 2H, CH2cyclopropyl), 1.27(m, 1H, cyclopropyl-CH), 2.93(t, 2H, β -CH2), 3.56(q, 2H, α-CH2), 3.85(s, 3H, OCH3), 5.72(br s, 1H, NH), 6.80-7.25(m, 3Harom), 8.21(br s, 1H, NHindole).

Workup

  1. temperaturecooled at 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with NaCl solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification
  7. customby flash chromatography (silica gel; ethyl acetate/cyclohexane 6:4) and crystallization

Sources & evidence

ORD record
ord-b4322439566142c59e6f769d4340b24a
Source dataset
uspto-grants-1996_09
Patent number
US05552428

Reaction notes

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