Dimethylamine → 1-[1-(diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamide

HRID 426088

Reaktionsgleichung

Reaktionsgleichung von HRID 426088
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18](O)=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][N:28](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:29].[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CNC.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]1([CH:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([N:28]([CH3:29])[CH3:27])=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 5

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 236589521-[1-(Diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid

Produkt 1

HCID 236589531-[1-(diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-[1-(Diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid (0.35 g, 0.9 mmol) was dissolved in DMF (8 mL) and to the solution were added TBTU (0.39 g, 1.2 mmol), DIPEA (0.21 mL, 1.2 mmol) and a solution of dimethylamine (3.0 mL, 2M in THF, 6 mmol). The mixture was stirred at RT for 14 h. An aqueous solution of NaHCO3 was added and the mixture was extracted three times with methylene chloride. The combined organic layers were washed with brine and dried over MgSO4. The solvent was removed by evaporation and the product was purified by reversed phase chromatography (C8) using acetonitrile and aqueous ammonium acetate solution (0.1 M) as eluent. There was obtained 0.20 g (59%) of 1-[1-(diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamide. 1H NMR (500 MHz, CDCl3): δ 1.6-2.0 (cm, 6H), 2.4-2.5 (m, 1H), 2.8 (m, 2H), 2.9-3.0 (m, 5H), 3.1 (s, 3H), 3.4 (t, 2H), 4.4 (s, 1H), 7.2 (t, 2H), 7.3 (t, 4H), 7.4 (d, 4H); LCMS: m/z 378 (M+1)+.

Aufarbeitung

  1. extractionthe mixture was extracted three times with methylene chloride
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed by evaporation
  5. customthe product was purified by reversed phase chromatography (C8)

Quellen und Nachweise

ORD-Eintrag
ord-f39b68eac6394999876f91dca8a54946
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106208B2

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