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

HRID 1773398Notes

Reaction equation

HRID 1773398 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-fad0e14b307e42ab8c66ee02658d7cf1
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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