Boron Trichloride → {4-[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone

HRID 393213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393213
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:28][CH2:29][CH3:30])[CH:14]3[CH2:19][CH2:18][N:17]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH2:16][CH2:15]3)[CH2:10]2)=[CH:5][CH:4]=1.B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:28][CH2:29][CH3:30])[CH:14]3[CH2:15][CH2:16][N:17]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH2:18][CH2:19]3)[CH2:10]2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 25135Boron TrichlorideHCID 10216398HCID 10216398, Verbindung

Produkt 1

HCID 22649552{4-[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanoneAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a −78° C. solution of {4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone (300 mg, 0.72 mmol) and tetrabutylammonium iodide (292 mg, 0.79mmol) in dichloromethane (20 mL) under an inert atmosphere was added boron trichloride (1M, 2.5 mL, 2.5 mmol) dropwise. The reaction was warmed to room temperature and stirred for 2.5 h. The reaction was quenched by slow addition of water and the organic layer separated and dried (MgSO4). This was concentrated onto silica (1.5 g) and placed on top of a flash column. Chromatography eluting with 30% acetone in hexanes afforded {4-[(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone (128 mg).

Aufarbeitung

  1. customThe reaction was quenched by slow addition of water
  2. customthe organic layer separated
  3. dry with materialdried (MgSO4)
  4. concentrationThis was concentrated onto silica (1.5 g)
  5. washChromatography eluting with 30% acetone in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-721952a74125458591d1240994bab434
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806278B2

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