Cyclopropylamine → (E)-N-cyclopropyl-2-(4,6-difluoro-1-indanylidene)acetamide

HRID 362826Notes

Reaction equation

HRID 362826 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[CH:12]\[C:13](Cl)=[O:14].[CH:16]1([NH2:19])[CH2:18][CH2:17]1>ClCCl>[CH:16]1([NH:19][C:13](=[O:14])/[CH:12]=[C:6]2\[CH2:5][CH2:4][C:3]3[C:7]\2=[CH:8][C:9]([F:11])=[CH:10][C:2]=3[F:1])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 10977254(E)-2-(4,6-difluoro-1-indanylidene)acetyl Chloride

Product 1

HCID 11747017(E)-N-cyclopropyl-2-(4,6-difluoro-1-indanylidene)acetamideYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice cold solution of (E)-2-(4,6-difluoro-1-indanylidene)acetyl chloride (2.97 g, 0.013 mol) in dichloromethane (30 mL) was treated with cyclopropylamine (1.48 g, 0.026 mol, Aldrich) and the mixture was stirred for 4 h. The mixture was concentrated in vacuo and the residue was taken up in a mixture of ethyl acetate and 5% aqueous sodium bicarbonate. The ethyl acetate phase was washed with 5% aqueous sodium bicarbonate, saturated aqueous NaCl and dried (Na2SO4). Chromatography on silica gel with ethyl acetate: hexanes (1:1) as eluent and trituration of the resulting solid with pentane gave 1.92 g (59%) of (E)-N-cyclopropyl-2-(4,6-difluoro-1-indanylidene)acetamide as a white solid: m.p., 156°-158° C.;

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was taken up in a mixture of ethyl acetate and 5% aqueous sodium bicarbonate
  3. washThe ethyl acetate phase was washed with 5% aqueous sodium bicarbonate, saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-4fff048d7b51455e992197e2ade2e506
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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