N-bromobutanimide → 3-(5-Bromo-2,3-dihydro-benzofuran-4-yl)-propylamine

HRID 1602383Notes

Reaction equation

HRID 1602383 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][NH2:14])[C:5]=2[CH2:4][CH2:3]1.[Br:15]N1C(=O)CCC1=O>C(O)(=O)C>[Br:15][C:9]1[CH:8]=[CH:7][C:6]2[O:2][CH2:3][CH2:4][C:5]=2[C:10]=1[CH2:11][CH2:12][CH2:13][NH2:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 196116703-(2,3-Dihydro-benzofuran-4-yl)-propylamine hydrochloride

Product 1

HCID 196116373-(5-Bromo-2,3-dihydro-benzofuran-4-yl)-propylamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the free base (200 mg) liberated from 3-(2,3-dihydro-benzofuran-4-yl)-propylamine hydrochloride and N-bromosuccinimide (215 mg) in acetic acid (5 ml) was stirred at room temperature overnight. The solution was evaporated to dryness and the residue taken up in water, basified to pH9-10 with 2N sodium hydroxide and extracted with ethyl acetate. The extracts were dried and evaporated to give the title compound (256 mg) as a pale yellow oil. Tic SiO2 (Dichloromethane/methanol/0.880 ammonia 75:8:1) Rf 0.53

Workup

  1. customThe solution was evaporated to dryness
  2. extractionextracted with ethyl acetate
  3. customThe extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-8162816dff3743df98aae48742dfd4f9
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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