2-(4-Aminophenyl)ethylamine → HCID 21190172, compound

HRID 619517Notes

Reaction equation

HRID 619517 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.C([O:22][C:23]([C:25]1[N:30]2[C:31]([C:34](=[O:39])C(Cl)(Cl)Cl)=[CH:32][N:33]=[C:29]2[CH:28]=[CH:27][CH:26]=1)=O)C>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:23](=[O:22])[C:25]3[N:30]4[C:31](=[CH:32][N:33]=[C:29]4[CH:28]=[CH:27][CH:26]=3)[C:34]2=[O:39])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 728952-(4-Aminophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 15472383HCID 15472383, compound

Product 1

HCID 21190172HCID 21190172, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1.63 g (12.0 mmol) of 2-[4-(amino)phenyl]ethylamine and 1.68 g (13 mmol) of N,N-diisopropylethylamine in 40 ml of acetonitrile was added a solution of 3.50 g (10.0 mmol) of 5-ethoxycarbonyl-3-trichloroacetylimidazo[1,2-a]pyridine in 10 ml of acetonitrile. The mixture was stirred for one hour at room temperature. The resulting crystalline precipitates were collected by filtration, washed with acetonitrile and dried to afford 1.03 g of the desired compound (33.6%, a yellow crystals). The filtrate was concentrated. The residne was crystallized from acetonitrile-methylene chloride. Crystalline precipitatse were collected by filtration, washed with acetonitrile to afford 1.60 g of the desired compound (52.1%, a yellow crystals).

Workup

  1. customThe resulting crystalline precipitates
  2. filtrationwere collected by filtration
  3. washwashed with acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-71f15d5cf8484a0f81d5729d3bcc2103
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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