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

HRID 263417Notes

Reaction equation

HRID 263417 reaction equation
C([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][CH2:8][C@@H:7]3C[C@H](N(CC4CC4)CC4CC4)C[C:5]=1[C:6]=23)(=O)C.C([N:27]([CH2:30]C)CC)C.ClC(Cl)(Cl)C[O:35]C(Cl)=O>C(Cl)Cl>[C:30]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)(=[O:35])[NH2:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 18654740(-) (2aR,4S)-6-acetyl-4-[di(cyclopropylmethyl)amino]-1,2,2a,3,4,5-hexahydrobenz[cd]indole

Product 1

HCID 7715242,3-dihydro-1H-indole-1-carboxamideYield 248.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (-)(2aR,4S)-6-acetyl-4-[di -(cyclopropylmethyl)amino]-1,2,2a,3,4,5-hexahydrobenz -[cd]indole (2.5 g, 7.7 mmol) and triethylamine (1.1 ml, 8 mmol) in 90 ml CH2Cl2 was added dropwise a solution of 2,2,2-trichloroethylchloroformate (1.7 g, 8 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 and a saturated brine solution, dried over MgSO4 and then concentrated to dryness in vacuo to give 3.1 g of the 1-carbamylindoline.

Workup

  1. extractionextracted with water and 1N HCl
  2. washThe organic solution was washed with a saturated NaHCO3 solution
  3. dry with materiala saturated brine solution, dried over MgSO4
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-52ba479bc8ac473382de59cdda950d00
Source dataset
uspto-grants-1997_07
Patent number
US05643910

Reaction notes

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