Chlorosuccinimide → 3-(5-Chloro-2,3-dihydro-benzofuran-4-yl)propylamine hydrochloride

HRID 1602397Notes

Reaction equation

HRID 1602397 reaction equation
[ClH:1].[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.[Cl:15]N1C(=O)CCC1=O>C(O)(=O)C>[ClH:15].[Cl:1][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 31398ChlorosuccinimideHCID 196116703-(2,3-Dihydro-benzofuran-4-yl)-propylamine hydrochloride

Product 1

HCID 196116663-(5-Chloro-2,3-dihydro-benzofuran-4-yl)propylamine hydrochlorideYield 91.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of of 3-(2,3-dihydro-benzofuran-4-yl)-propylamine hydrochloride (150 mg) and N-chlorosuccinimide (100 mg) in acetic acid (50 ml) was stirred at room temperature overnight. The solution was evaporated to dryness and the residue taken up in water, basified with 2N sodium hydroxide and extracted with dichloromethane. The extracts were dried and evaporated and the residue disolved in a solution of hydrogen chloride in methanol. Evaporation gave the the title compound (159 mg) as an off-white powder after trituration with ether.

Workup

  1. customThe solution was evaporated to dryness
  2. extractionextracted with dichloromethane
  3. customThe extracts were dried
  4. customevaporated
  5. customEvaporation

Sources & evidence

ORD record
ord-63f4c3f878b44de49201f7f2c813e6b7
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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