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

HRID 1777526ノート

反応式

HRID 1777526 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9092e4da988349d38bb0ad4659c1b56e
出典データセット
uspto-grants-2016_02
特許番号
US09266832B2

反応ノート

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