Piperidine → 2-Nitro-4-(piperidine-1-carbonyl)-benzoic acid tert-butyl ester

HRID 2068793Notes

Reaction equation

HRID 2068793 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2].O[N:21]1[C:25]2C=[CH:27][CH:28]=[CH:29][C:24]=2N=N1.CCN=C=NCCCN(C)C.N1CCCCC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([N:21]2[CH2:27][CH2:28][CH2:29][CH2:24][CH2:25]2)=[O:13])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 686717752-Nitro-terephthalic acid 1-tert-butyl ester

Product 1

HCID 686720862-Nitro-4-(piperidine-1-carbonyl)-benzoic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Nitro-terephthalic acid 1-tert-butyl ester (500 mg, 1.88 mmol) in DCM (18 mL), was treated with 1-hydroxybenzotriazole (0.39 g, 2.43 mmol), EDCI (0.47 g, 2.43 mmol) and piperidine (0.24 mL, 2.43 mmol). After 3 hours the reaction was diluted with DCM (50 mL) and washed with aqueous NaHCO3 (30 mL), water (30 mL) and finally with brine. After drying over sodium sulphate and evaporation of the solvent the title compound was obtained as a colourless oil in quantitative yield. The crude was employed in the following reaction without any further purification.

Workup

  1. washwashed with aqueous NaHCO3 (30 mL), water (30 mL) and finally with brine
  2. dry with materialAfter drying over sodium sulphate and evaporation of the solvent the title compound
  3. customwas obtained as a colourless oil in quantitative yield
  4. customThe crude was employed in the following reaction without any further purification

Sources & evidence

ORD record
ord-f5f074112d39463f8e6c216ffd9d964c
Source dataset
uspto-grants-2012_10
Patent number
US08299057B2

Reaction notes

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