Sodium Hydroxide → HCID 70473200, compound

HRID 2278659Notes

Reaction equation

HRID 2278659 reaction equation
C([BH3-])#N.[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2.[OH-].[Na+]>FC(F)(F)C(O)=O.O>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][NH:16]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22561694HCID 22561694, compound

Product 1

HCID 70473200HCID 70473200, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

558 g of sodium cyanoborohydride are added in portions to a suspension of 960 mg of 4-(2-chlorophenyl)-1H-indole in 11 ml of trifluoroacetic acid cooled to 0° C. The reaction medium is stirred for 16 hours while allowing it to rise to ambient temperature and then the pH is brought to neutrality with a sodium hydroxide solution. The reaction mixture is diluted with 300 ml of water then extracted with ethyl acetate (2×250 ml). The organic phases are combined and then concentrated to dryness under reduced pressure. After purification of the residue by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (80/20), 395 mg of 4-(2-chlorophenyl)-2,3-dihydro-1H-indole are obtained in the form of a colorless viscous oil.

Workup

  1. customto rise to ambient temperature
  2. extractionthen extracted with ethyl acetate (2×250 ml)
  3. concentrationconcentrated to dryness under reduced pressure
  4. customAfter purification of the residue
  5. washby silica column chromatography, elution
  6. additionbeing carried out with a mixture of heptane and ethyl acetate (80/20), 395 mg of 4-(2-chlorophenyl)-2,3-dihydro-1H-indole
  7. customare obtained in the form of a colorless viscous oil

Sources & evidence

ORD record
ord-e69f6306a36f4c5999a9291470048ec9
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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