Water → N-{2-[4(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-3-methoxybenzamide

HRID 968765Notes

Reaction equation

HRID 968765 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH2:14])[CH2:8][CH2:7]1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=[O:32].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][NH:14][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][CH:36]=[C:28]([O:27][CH3:26])[CH:29]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 113582094-(3,4-Dichlorophenoxy)-1-piperidineethanamine

Product 1

HCID 9910169N-{2-[4(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-3-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 3, Step b (2.00 g) was dissolved in TBF (100 ml) and triethylamine (2.10 g) added. The solution was then cooled with stirring to 0° C. and to it 3-methoxybenzoyl chloride was added dropwise as a solution in THF (10 ml). Reaction was left to warm to room temp and left for 24 hours then water was added and the organics extracted into ethyl acetate. The combined organics were dried with MgSO4 and the solvent removed by evaporation. The crude product was purified by flash chromatography to leave the sub-title product as a pale yellow oil (1.38 g).

Workup

  1. temperatureThe solution was then cooled
  2. customReaction
  3. waitwas left
  4. extractionthe organics extracted into ethyl acetate
  5. dry with materialThe combined organics were dried with MgSO4
  6. customthe solvent removed by evaporation
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-4ea4457e9599494bbd3bb90bc955551f
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

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