Dichloromethane → Ammonia dichloromethane

HRID 33729

Reaktionsgleichung

Reaktionsgleichung von HRID 33729
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:49]([Cl:51])[Cl:50]>C(O)(=O)C>[NH3:1].[CH2:49]([Cl:51])[Cl:50].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:27][CH2:28][N:29]([CH2:15][C:14]3[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:12][CH:13]=3)[CH2:30][CH2:31]2)=[CH:22][CH:21]=1

Komponenten

8

Edukt 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 2

HCID 102751974-(4-Chloro-phenyl)-1-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperidin-4-olHCID 22731429Ammonia dichloromethaneAusbeute 1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of the product of Example 9 (200 mg), 4-(4-chloro-phenyl)-piperidin-4-ol (170 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (300 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (203 mg). 1H NMR (400 MHz, CDCl3): 7.46-7.42 (m, 2H), 7.32-7.28 (m, 2H), 7.25-7.22 (m, 2H), 6.87-6.84 (m, 2H), 3.99 (t, J=6.3 Hz, 2H), 3.51 (s, 2H), 2.78 (m, 2H), 2.51-2.36 (m, 8H), 2.11 (m, 2H), 1.98 (m, 2H), 1.69 (m, 2H), 1.63-1.56 (m, 4H), 1.48-1.40 (m, 2H).

Aufarbeitung

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e7a26bc770294d2fa0b9d2f95f59c354
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429586B2

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