4-Methylbenzoyl Chloride → HCID 20718668, compound

HRID 1610894Notes

Reaction equation

HRID 1610894 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C@@H:23]([NH2:27])[CH:24]([CH3:26])[CH3:25])[CH2:18][CH2:17]1>N1C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:15][CH:16]1[CH2:17][CH2:18][N:19]([CH2:22][C@@H:23]([NH:27][C:7](=[O:8])[C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)[CH:24]([CH3:26])[CH3:25])[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 18346053HCID 18346053, compound

Product 1

HCID 20718668HCID 20718668, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

p-Toluoyl chloride (0.14 ml, 1 mmol) was added to a solution of 1-(S)-[4-(3,4-dichlorobenzyl)piperidin-1-ylmethyl]-2-methylpropylamine (0.33 g, 1 mmol) in dry pyridine (7 ml) at 0° C. under argon atmosphere. The solution was stirred for 30 min., at 0° C. and then allowed to warm to room temperature. After 3 h, the reaction mixture was concentrated under reduced pressure and water (10 ml) was added. The product was extracted with ethyl acetate and the organic layer was dried with magnesium sulfate and then concentrated in vacuo. The crude product (0.5 g) was chromatographed by eluting with a gradient of from 1% to 4% methanol/methylene chloride to give N-{1-(S)-[4-(3,4-dichlorobenzyl)piperidin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide (0.25 g) as partially solidified gum.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 3 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure and water (10 ml)
  4. additionwas added
  5. extractionThe product was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product (0.5 g) was chromatographed
  9. washby eluting with a gradient of from 1% to 4% methanol/methylene chloride

Sources & evidence

ORD record
ord-57ae79422c5a4cbf98445abfd482656b
Source dataset
uspto-grants-2006_01
Patent number
US06984637B2

Reaction notes

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