Acetic Anhydride → N-[2-(6-Fluoro-1H-indol-3-yl)-ethyl]-acetamide

HRID 1432456Notes

Reaction equation

HRID 1432456 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][CH2:12][NH2:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.CCN(CC)CC.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][CH2:12][NH:13][C:21](=[O:23])[CH3:22])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8540242-(6-fluoro-1H-indol-3-yl)ethanamine

Product 1

HCID 10751398N-[2-(6-Fluoro-1H-indol-3-yl)-ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(6-fluoro-1H-indol-3-yl)-ethylamine (0.88 g) and NEt3 (2.27 ml) in CH2Cl2 (8 ml) was added acetic acid anhydride (0.43 ml) and stirring was continued at 22° C. for 1 h. The mixture was washed with 1 N aqueous HCl, the organic layer was dried and evaporated. The residue was chromatographed on silica using CH2Cl2/MeOH (25:1) to give the title compound as a pale yellow oil. MS: 219.1 ([M−H]−).

Workup

  1. washThe mixture was washed with 1 N aqueous HCl
  2. customthe organic layer was dried
  3. customevaporated
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-432ce235113849a9b02b18ec2bd39310
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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