N-Methylbenzylamine → HCID 19085462, compound

HRID 962463Notes

Reaction equation

HRID 962463 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16]Cl)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][N:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:18])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7669N-MethylbenzylamineHCID 19085432HCID 19085432, compound

Product 1

HCID 19085462HCID 19085462, compound

Procedure

A mixture of 1-benzoyl-4-(2-chloroethyl)piperidine (11.61 g), N-methylbenzylamine (16.75 g) and IMS (100 ml) was boiled under reflux for 16 hours. The mixture was evaporated to dryness and then 4M hydrochloric acid (50 ml) was added to the residue. The mixture was washed with ether and the acidic layer was then basified with 4M sodium hydroxide solution and extracted with dichloromethane to give an oil. Excess amine was distilled off at 13 mbar and the residue was triturated with petroleum ether b.p. 40°-60° C. The supernatant petroleum ether was decanted off and the residual oil was dried under vacuum to give 1-benzoyl-4-[2-(N-benzyl-N-methylamino)ethyl]piperidine. A small portion of the oil was dissolved in ether and acidified with ethereal oxalic acid. The supernatant liquid was decanted off and the solid residue was triturated with acetone and filtered to give the oxalate salt, m.p. 141°-142° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe mixture was evaporated to dryness
  3. addition4M hydrochloric acid (50 ml) was added to the residue
  4. washThe mixture was washed with ether
  5. extractionextracted with dichloromethane
  6. customto give an oil
  7. distillationExcess amine was distilled off at 13 mbar
  8. customthe residue was triturated with petroleum ether b.p. 40°-60° C
  9. customThe supernatant petroleum ether was decanted off
  10. customthe residual oil was dried under vacuum

Sources & evidence

ORD record
ord-eb89f4daadc94529b3136ade9359c630
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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