Triethylamine → 2,2-Dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

HRID 249328Notes

Reaction equation

HRID 249328 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1.CCN(CC)CC>C(Cl)Cl>[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 197614202-(2-Aminophenyl)-2,3-dihydro-1H-indole

Product 1

HCID 197613982,2-Dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylacetyl chloride (3.6 ml) was added dropwise to a solution of 5.8 g 2-(2-aminophenyl)-2,3-dihydro-1H-indole and 4.3 ml Et3N in 75 ml CH2Cl2 with ice bath cooling. The resulting mixture was stirred at room temperature for thirty minutes and then quenched with water. The organic extract was washed with water, saturated NaHCO3 solution and saturated NaCl solution and dried (MgSO4). Concentration gave 7.7 g crude product which was flash chromatographed using CH2Cl2 as eluent to give 4.9 g solid, m.p. 175°-178° C.

Workup

  1. temperaturecooling
  2. customquenched with water
  3. extractionThe organic extract
  4. washwas washed with water, saturated NaHCO3 solution and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration
  7. customgave 7.7 g crude product which
  8. customchromatographed

Sources & evidence

ORD record
ord-88f6ffffef93490b8b8fcdd8d93b0e51
Source dataset
uspto-grants-1993_05
Patent number
US05214059

Reaction notes

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