Hydrochloric Acid → 2-(4-Ethoxyphenyl)-n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)acetamide

HRID 929737Notes

Reaction equation

HRID 929737 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1)[CH3:18].Cl.CCCCCCC>ClCCl>[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[O:28])=[CH:22][CH:21]=1)[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8900HeptaneHCID 28466454-(4-Fluorobenzylamino)-1-methylpiperidineHCID 116297822-(4-ethoxyphenyl)acetyl Chloride

Product 1

HCID 102934182-(4-Ethoxyphenyl)-n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50ELH4 (0.11 g, 0.49 mmol, 1.0 eq.) was transferred to a 4 ml vial and dissolved in dichloromethane. 63ELH19 (0.089 mg, 1.0 eq.) was added and the vial was sealed and the reaction shaken for 20 h. The product was extracted in distilled water (made basic with potassium carbonate, pH 10) and dichloromethane. Dried with sodium sulfate and concentrated. Purified by HPLC. The extraction, drying and concentration was repeated and the product dissolved in dichloromethane (1 ml) and HCl (1 eq., 2 M in ether) is added. This mixture was added drop-wise to an excess of heptane whereupon the salt precipitated. Yield 31.1 mg (16%), UV/MS: 94/100 (M+ 385), tr (A, MS) 2.573.

Workup

  1. customthe vial was sealed
  2. extractionThe product was extracted in distilled water (made basic with potassium carbonate, pH 10)
  3. dry with materialDried with sodium sulfate
  4. concentrationconcentrated
  5. customPurified by HPLC
  6. extractionThe extraction
  7. customdrying
  8. concentrationconcentration
  9. dissolutionthe product dissolved in dichloromethane (1 ml)
  10. customprecipitated

Sources & evidence

ORD record
ord-d75d849d8c904d44bf24d92fa1a25bba
Source dataset
uspto-grants-2016_03
Patent number
US09296694B2

Reaction notes

Loading…