Dimethylformamide → N-cyclohexyl-2-nitro-4-(piperidin-1-ylmethyl)aniline

HRID 2068298Notes

Reaction equation

HRID 2068298 reaction equation
OC(C(F)(F)F)=O.F[C:9]1[CH:21]=[CH:20][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:11][C:10]=1[N+:22]([O-:24])=[O:23].[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)C(C)C)(C)C.CN(C)C=O>C(OCC)(=O)C>[CH:25]1([NH:31][C:9]2[CH:21]=[CH:20][C:12]([CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:11][C:10]=2[N+:22]([O-:24])=[O:23])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 866547931-(4-Fluoro-3-nitro-benzyl)-piperidine-TFA salt

Product 1

HCID 46735183N-cyclohexyl-2-nitro-4-(piperidin-1-ylmethyl)anilineYield 140.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Fluoro-3-nitro-benzyl)-piperidine—TFA salt (2.69 g, 0.00764 mol), cyclohexanamine (3.87 mL, 0.0339 mol) and N,N-Diisopropylethylamine (6.00 mL, 0.0344 mol) were dissolved in N,N-dimethylformamide (8.00 mL, 0.103 mol). The mixture was apportioned into four vials and each was microwaved at 300 watts, 130° C. for 7 minutes. The combined reaction mixtures were diluted with ethyl acetate, washed with 5% citric acid, saturated sodium chloride, dried over sodium sulfate and concentrated to give 3.40 g of the title compound as the citrate salt.

Workup

  1. customeach was microwaved at 300 watts, 130° C. for 7 minutes
  2. customThe combined reaction mixtures
  3. washwashed with 5% citric acid, saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7691657e3d9f4c9abf7d20c4bfad29a2
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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