1H-Indole, 2-propyl- → 2-Propylindoline

HRID 1640253Notes

Reaction equation

HRID 1640253 reaction equation
C([BH3-])#N.[Na+].[CH2:5]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH3:7]>C(O)(=O)C>[CH2:5]([CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9]1)[CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 1394151H-Indole, 2-propyl-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 127154212-Propylindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.3 g (20 mmol) sodium cyanoborohydride were added to 0.75 g (4.7 mmol) 2-propyl-1H-indole in 10 mL conc. acetic acid and the mixture was stirred for 5 h at RT. The reaction mixture was evaporated down. The residue was mixed with 20 mL of a 4N HCl solution and stirred for 1 h at RT. Then 45 mL of a 4N sodium hydroxide solution was slowly added while cooling with ice and the mixture was extracted with ethyl acetate. The organic phase was dried on sodium sulphate and evaporated down.

Workup

  1. customThe reaction mixture was evaporated down
  2. additionThe residue was mixed with 20 mL of a 4N HCl solution
  3. stirringstirred for 1 h at RT
  4. additionThen 45 mL of a 4N sodium hydroxide solution was slowly added
  5. temperaturewhile cooling with ice
  6. extractionthe mixture was extracted with ethyl acetate
  7. customThe organic phase was dried on sodium sulphate
  8. customevaporated down

Sources & evidence

ORD record
ord-eb15c031a080473394cf867f15512c1b
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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