Water → 3-(5-chloro-1H-indol-3-yl)propan-1-amine

HRID 925308Notes

Reaction equation

HRID 925308 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=2)[NH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Cl:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:6][CH2:5][CH2:4][NH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866993903-(3-azidopropyl)-5-chloro-1H-indole

Product 1

HCID 16364293-(5-chloro-1H-indol-3-yl)propan-1-amineYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-Azidopropyl)-5-chloro-1H-indole (0.299 g; 1.27 mmol) in THF (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then concentrated under reduced pressure. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2×10 mL) and the pH was adjusted to 14 with an aqueous solution of sodium hydroxide 6N. This basic solution was extracted dichloromethane (3×20 mL) and the combined organic layer was dried over magnesium sulphate, and evaporated to afford 0.089 g (34%) of 3-(5-Chloro-1H-indol-3-yl)propan-1-amine as a white solid.

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (10 mL)
  3. addition10 mL of 6N hydrochloric acid were added
  4. customAfter separation
  5. extractionthe aqueous layer was further extracted with dichloromethane (2×10 mL)
  6. extractionThis basic solution was extracted dichloromethane (3×20 mL)
  7. dry with materialthe combined organic layer was dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-48c73b7f25164996afa754e259bf1daf
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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