Ethylenediamine → HCID 18476352, compound

HRID 2187645Notes

Reaction equation

HRID 2187645 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]([O:14]CC)=O)=[CH:8][C:7]([CH3:17])=[CH:6][CH:5]=2.[CH2:18]([NH2:21])[CH2:19][NH2:20]>>[NH2:20][CH2:19][CH2:18][NH:21][C:12](=[O:14])[CH2:11][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:17])[CH:8]=2)[NH:3][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 12547842HCID 12547842, compound

Product 1

HCID 18476352HCID 18476352, compoundYield 39%

Conditions

Temperature
115 °C

Procedure

A mixture of 1.18 g (4.8 mmol) of ethyl (2,5-dimethylindol-3-yl)acetate and 7.5 mL of ethylenediamine was heated at 115° C. overnight. The excess ethylenediamine was removed under reduced pressure and the residue was chromatographed with 1:1 CH2Cl2-(EtOH+10% ethanolic NH3). The pure fraction of N-(2-aminoethyl)-(2,5-dimethylindol-3-yl)acetamide obtained (1.2 g) was treated with 15 mL of hexamethyldisilazine HDS) at gentle reflux (130° C.) overnight. The mixture was concentrated to dryness, dissolved in EtOH and treated with etheric HCl to acidic. Addition of ether in 3 portions induced light brown crystals. Yield: 39%; m.p. 245-7° C.; 1H NMR (DMSO-d6) d 11.02 (br. s, 1H), 9.94 (br. s, 2H), 7.23 (s, 1H ), 7.16 (d, J=8.0 Hz, 1H), 6.85 (d, J=8.0 Hz, 1H), 3.90 (s, 2H), 3.79 (s, 4H), 2.36 (s, 6H).

Workup

  1. customThe excess ethylenediamine was removed under reduced pressure
  2. customthe residue was chromatographed with 1:1 CH2Cl2-(EtOH+10% ethanolic NH3)

Sources & evidence

ORD record
ord-037f7ec984b840509694908910a34999
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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