Triethylamine → 2,3-dihydro-1H-indole-1-carboxamide

HRID 5427

Reaction equation

HRID 5427 reaction equation
C([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][CH2:8][CH:7]3CC(N(CCC)CCC)C[C:5]=1[C:6]=23)(=O)C.C([N:25]([CH2:28]C)CC)C.ClC(OCC(Cl)(Cl)Cl)=[O:32]>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:32])[NH2:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 9839315(+)-6-Acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

Product 1

HCID 7715242,3-dihydro-1H-indole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. extractionThe CH2Cl2 solution was extracted with water and 1N HCl
  2. washThe organic solution was washed with saturated NaHCO3 solution and with brine solution
  3. dry with materialThe CH2Cl2 solution was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39c6db17ee584deba9aaa702687d55e0
Source dataset
uspto-grants-1993_09
Patent number
US05244911

Linked notes

Loading…