Triethylamine → 2,3-dihydro-1H-indole-1-carboxamide
Reaction equation
C([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][CH2:8][C@H:7]3C[C@@H](N(CCC)CCC)C[C:5]=1[C:6]=23)(=O)C.C([N:25]([CH2:28]C)CC)C.ClC(Cl)(Cl)C[O:33]C(Cl)=O>C(Cl)Cl>[C:28]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)(=[O:33])[NH2:25]Participants
5
Procedure
To a solution of (+)(2aS,4R)-6-acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (1.7 g, 5.7 mmol) and triethylamine (0.8 ml, 6 mmol) in 90 ml CH2Cl2 was added dropwise a solution of 2,2,2-trichloroethylchloroformate (1.3 g, 6 mmol) in 10 ml CH2Cl2. The reaction mixture was stirred at room temperature for one hour and then extracted with water and 1N HCl. The organic solution was washed with a saturated NaHCO3 solution, a saturated brine solution, dried over MgSO4 and then concentrated to dryness in vacuo to give 2.5 g of the 1-carbamylindoline.
Workup
- extractionextracted with water and 1N HCl
- washThe organic solution was washed with a saturated NaHCO3 solution
- dry with materiala saturated brine solution, dried over MgSO4
- concentrationconcentrated to dryness in vacuo
Sources & evidence
- ORD record
- ord-4759f96742e4405d80aa7044ee4bf327
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05624944
Reaction notes
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