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

HRID 57574

Reaction equation

HRID 57574 reaction equation
[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]

Participants

7

Reactant 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)

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-50e724b041f8481db32ad1c93d67fdcd
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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