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

HRID 1777526Notes

Reaction equation

HRID 1777526 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>O1CCCC1>[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 tetrahydrofuran (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 evaporated to dryness. 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 a solution of sodium hydroxide 6N. This basic solution was extracted with dichloromethane (3×20 mL) and the combined organic layer was dried over magnesium sulfate, 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. customwas then evaporated to dryness
  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 with dichloromethane (3×20 mL)
  7. dry with materialthe combined organic layer was dried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-9092e4da988349d38bb0ad4659c1b56e
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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