Propargylamine → HCID 22285037, compound

HRID 984845Notes

Reaction equation

HRID 984845 reaction equation
Cl[C:2]1[C:3]([Cl:16])=[N:4][C:5]2[CH:6]=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][C:10]=2[N:11]=1.[CH2:17]([NH2:20])[C:18]#[CH:19]>O1CCOCC1>[Cl:16][C:3]1[C:2]([NH:20][CH2:17][C:18]#[CH:19])=[N:11][C:10]2[CH:9]=[C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]3=[CH:6][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 9942937HCID 9942937, compound

Product 1

HCID 22285037HCID 22285037, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,3-dichlorobenzo[g]quinoxaline (0.634 g, 2.55 mmol), propargylamine (0.21 ml, 3.05 mmol) and TEA (0.53 mL, 3.83 mmol) in 15 mL of dioxane was heated to reflux for 4.5 hours. After evaporating the resulting mixture under vacuum, the crude product was chromatographed (CH2Cl2) to afford the title compound as a yellow solid (0.496 g, 73%); mp 169-172° C.; IR (KBr, cm−1) 3412, 3283, 3235, 1570, 1508, 1335; 1H NMR (DMSO) δ 8.44 (s, 1H), 8.26 (s, 1H), 8.16-8.06 (m, 3H), 7.58-7.54 (m, 1H), 7.51-7.48 (m, 1H), 4.28 (dd, J=6.1, 2.5, 2H), 3.12 (t, J=2.5, 1H); LC/MS 97.8% (220 nm), m/z (M+H+) 268.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 hours
  3. customAfter evaporating the resulting mixture under vacuum
  4. customthe crude product was chromatographed (CH2Cl2)

Sources & evidence

ORD record
ord-e26fb7061165435e80506cd755aa4c2b
Source dataset
uspto-grants-2005_03
Patent number
US06869956B2

Reaction notes

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