1,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylate → HCID 68513365, compound

HRID 1716593Notes

Reaction equation

HRID 1716593 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]>C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=3[N:22]=[C:6]2[O:5][CH2:1][CH3:2])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

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

Product 1

HCID 68513365HCID 68513365, compoundYield 173%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(2-Amino-4-methylphenylamino)-piperidine-1-carboxylic acid tert-butyl ester (361 mg, 1.18 mmol) was mixed with tetraethyl carbonate (272 mg, 1.20 eq) in 4 mL of acetic acid. The mixture was stirred at r.t for 4 hrs until all starting material was consumed. The solution was evaporated and the residue was extracted with ethyl acetate and concentrated NaHCO3 solution. The organic layer was dried and solvents were evaporated. The resulting residue was purified on a Biotage flash column chromatography using ethyl acetate and hexanes (1:2 ratio) to give 4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (367 mg, 86%) as an oil. ES-MS showed m/e 360 (M++1). 1H-NMR (CDCl3) δ 7.33 (s, 1H), 7.10 (d, 1H), 6.92 (d, 1H), 4.58 (q, 2H), 4.23-4.33 (m, 3H), 2.83 (t, 2H), 2.41 (s, 3H), 2.25-2.31 (m, 2H), 1.82 (d, 2H), 1.49 (s, 9H), 1.46 (t, 3H).

Workup

  1. customwas consumed
  2. customThe solution was evaporated
  3. extractionthe residue was extracted with ethyl acetate and concentrated NaHCO3 solution
  4. customThe organic layer was dried
  5. customsolvents were evaporated
  6. customThe resulting residue was purified on a Biotage flash column chromatography

Sources & evidence

ORD record
ord-9cf12cbf5063438cad0f48c40a1a8c86
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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