4-Nitrophenyl 2,2-diethoxypropanoate → HCID 68510828, compound

HRID 1716576Notes

Reaction equation

HRID 1716576 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH2:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:25][C:26]([O:40][CH2:41][CH3:42])([CH3:39])[C:27](OC1C=CC([N+]([O-])=O)=CC=1)=[O:28])[CH3:24]>CN(C1C=CN=CC=1)C.C(#N)C.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH:22][C:27](=[O:28])[C:26]([O:40][CH2:41][CH3:42])([O:25][CH2:23][CH3:24])[CH3:39])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 138072334-Nitrophenyl 2,2-diethoxypropanoateHCID 588522881,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylate

Product 1

HCID 68510828HCID 68510828, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

4-(2-Amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (400 mg, 1.31 mmol), p-nitrophenyl 2,2-diethoxyproprionate (1.00 g, 3.50 mmol), and DMAP (1.00 g, 8.2 mmol) were combined in acetonitrile (3 mL) and heated in an oil bath at 80° C. for 2 h. The mixture was cooled, diluted with diethyl ether (100 mL), washed once each with saturated aqueous NH4Cl and water, three times with 5% aqueous sodium hydroxide solution, once with brine and dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was adsorbed on a silica gel pad, and the pad was eluted with 25% ethyl acetate in hexanes to give 4-[2-(2,2-diethoxy-propionylamino)-4-methyl-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (550 mg, 0.81 mmol, 62%) of a pale yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed once each with saturated aqueous NH4Cl and water, three times with 5% aqueous sodium hydroxide solution
  3. dry with materialonce with brine and dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washthe pad was eluted with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-44aa94696a0c49c28e957422a891ee39
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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