Reaction #5523

Reaction equation

(±)-6-acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

triethylamine

2,2,2-trichloroethyl chloroformate

→

1-carbamylindoline

Solvents

CH2Cl2

Conditions

Workup

1. 1
   ExtractionThe CH2Cl2 solution was extracted with water and 1N HCl
2. 2
   WashThe organic solution was washed with saturated NaHCO3 solution and with brine solution
3. 3
   DryingThe CH2Cl2 solution was dried (MgSO4)
4. 4
   Concentrationconcentrated in vacuo

Procedure

To a solution of (±)-6-acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (2.3 g, 7.7 mmol) and triethylamine (1.1 ml, 8 mmol) in 90 ml CH2Cl2 under N2 was added dropwise a solution of 2,2,2-trichloroethyl chloroformate. The reaction mixture was stirred at RT for 1 hr. The CH2Cl2 solution was extracted with water and 1N HCl. The organic solution was washed with saturated NaHCO3 solution and with brine solution. The CH2Cl2 solution was dried (MgSO4) and concentrated in vacuo to give 3.3 g of the 1-carbamylindoline.

Source