(2-Thienylmethyl)amine → 2-(Pyrrolodin-2-one-1-ylmethyl)thiophene

HRID 52187

Reaction equation

HRID 52187 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7]CC)=O.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][NH2:16].C(N(CC)C(C)C)(C)C>C1C=CC=CC=1>[N:16]1([CH2:15][C:11]2[S:10][CH:14]=[CH:13][CH:12]=2)[CH2:2][CH2:3][CH2:4][C:5]1=[O:7]

Participants

5

Reactant 3

HCID 34005(2-Thienylmethyl)amineHCID 76300Ethyl 4-bromobutyrateHCID 81531Diisopropylethylamine

Product 1

HCID 675888032-(Pyrrolodin-2-one-1-ylmethyl)thiopheneYield 47.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of ethyl 4-bromobutyrate (5.85 g, 30.0 mmol), 2-thiophenemethylamine (13.6 g, 120 mmol), and N,N-diisopropylethylamine (3.88 g, 30.0 mmol) in benzene (100 mL) was stirred under N2 at reflux for 2 hours. The reaction mixture was cooled to ambient temperature and filtered. The residue was concentrated in vacuo, dissolved in ether, and washed twice with 2N aqueous HCl, and once with brine, then dried over MgSO4, filtered, and concentrated in vacuo to give 2-(pyrrolodin-2-one-1-ylmethyl)thiophene (2.59 g) as an oil.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationfiltered
  3. concentrationThe residue was concentrated in vacuo
  4. dissolutiondissolved in ether
  5. washwashed twice with 2N aqueous HCl
  6. dry with materialonce with brine, then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c48b2d98f97457b9551f2e75bdadaf4
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Linked notes

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