Hydrochloric Acid → N-[3-(5-Bromo-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

HRID 1602407Notes

Reaction equation

HRID 1602407 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[CH2:11][CH2:12][CH2:13][NH2:14].[C:15](OC(=O)C)(=[O:17])[CH3:16].Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 196116373-(5-Bromo-2,3-dihydro-benzofuran-4-yl)-propylamine

Product 1

HCID 19611695N-[3-(5-Bromo-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(5-bromo-2,3-dihydro-benzofuran-4-yl)-propylamine (256 mg) in pyridine (3 ml) at 40 was treated with acetic anhydride (0.11 ml) and the solution stored overnight at 4°. The cold solution was acidified with 2N hydrochloric acid and the mixture extracted with ethyl acetate. The extracts were dried and evaporated and the residue chromatographed on silica (20 g) using dichloromethane:methanol:ammonia (100:8:1) to give the title compound as an oil which slowly solidified (175 mg).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. customThe extracts were dried
  3. customevaporated
  4. customthe residue chromatographed on silica (20 g)

Sources & evidence

ORD record
ord-f16a92737d6e4f218c5560f825517973
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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