Dimethylformamide → N-2-(4-nitrophenoxy)ethyl-4-(4-nitrophenoxy)piperidine

HRID 1656596Notes

Reaction equation

HRID 1656596 reaction equation
Cl.[N+:2]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].Br[CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(Cl)Cl>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][N:13]2[CH2:12][CH2:11][CH:10]([O:9][C:8]3[CH:16]=[CH:17][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=3)[CH2:15][CH2:14]2)=[CH:23][CH:24]=1)([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2359871-(2-Bromoethoxy)-4-nitrobenzeneHCID 225914014-(4-Nitrophenoxy)piperidine hydrochloride

Product 1

HCID 19788723N-2-(4-nitrophenoxy)ethyl-4-(4-nitrophenoxy)piperidineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(4-nitrophenoxy)piperidine hydrochloride (1.15 g, 5.80 mmol), 1-bromo-2-(4-nitrophenoxy)ethane (1.43 g, 5.80 mmol), K2CO3 (1.60 g, 11.80 mmol), and DMF (15 mL) was heated at 90° C. for 6 hours. The mixture was cooled, diluted with CH2Cl2, and washed with water. The organic phase was dried (MgSO4) and concentrated to give 1.70 g (80%) of N-2-(4-nitrophenoxy)ethyl-4-(4-nitrophenoxy)piperidine as a yellow solid. 1H NMR (DMSO-d6): δ 8.10 (m, 4H), 7.05 (d, 4H), 4.60 (m, 1H), 4.15 (t, 2H), 2.78 (m, 4H), 2.40 (t, 2H), 1.95 (m, 2H), 1.65 (m, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f4a687344b824e449e7b500a083f4aae
Source dataset
uspto-grants-1993_10
Patent number
US05254689

Reaction notes

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