Dimethylamine → N,N-dimethyl-1-(4-nitrophenyl)piperidine-4-carboxamide

HRID 57574

Reaktionsgleichung

Reaktionsgleichung von HRID 57574
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:19]([CH3:21])[CH3:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.O>[CH3:20][N:19]([CH3:21])[C:16]([CH:13]1[CH2:12][CH2:11][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:15][CH2:14]1)=[O:18]

Komponenten

7

Edukt 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 27672651-(4-Nitrophenyl)piperidine-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 16370119N,N-dimethyl-1-(4-nitrophenyl)piperidine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-(4-nitrophenyl)piperidine-4-carboxylic acid, (CH3)2NH (2.37 g, 29.06 mmol), HATU (11.05 g, 29.06 mmol) and DIPEA (7.51 g, 58.12 mmol) in 30 mL of THF, was stirred at room temperature overnight. The mixture was added to 20 mL of water, extracted with EA, washed with water and brine, dried over Na2SO4. The volatiles were removed in vacuo to give 4.2 g of N,N-dimethyl-1-(4-nitrophenyl)piperidine-4-carboxamide. MS (m/z)=278 (M+H)+.

Aufarbeitung

  1. extractionextracted with EA
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customThe volatiles were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-50e724b041f8481db32ad1c93d67fdcd
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434726B2

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