Dichloromethane → Ammonia dichloromethane

HRID 33726

Reaktionsgleichung

Reaktionsgleichung von HRID 33726
[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.[CH3:19][NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:45]([Cl:47])[Cl:46]>C(O)(=O)C>[NH3:1].[CH2:45]([Cl:47])[Cl:46].[CH3:19][N:20]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1

Komponenten

8

Edukt 5

HCID 6344DichloromethaneHCID 11503N-MethylbenzeneethanamineHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 2

HCID 10133527Methyl-phenethyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amineHCID 22731429Ammonia dichloromethaneAusbeute 1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of the product of Example 9 (208 mg), methyl-phenethyl-amine (113 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 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 (300 mg). 1H NMR (400 MHz, CDCl3): 7.30-7.25 (m, 2H), 7.21-7.16 (m, 5H), 6.83 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.3 Hz, 2H), 3.49 (s, 2H), 2.84-2.79 (m, 2H), 2.65-2.62 (m, 2H), 2.51-2.37 (m, 6H), 2.26 (s, 3H), 1.98 (m, 2H), 1.63-1.56 (m, 4H), 1.47-1.40 (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-4b54ea5fb64f4c08af727180f78627ba
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429586B2

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