N-Ethyl-N-4-piperidinylacetamide → HCID 19761220, compound

HRID 2082355Notes

Reaction equation

HRID 2082355 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]([CH2:11][CH3:12])[C:8](=[O:10])[CH3:9])[CH2:3][CH2:2]1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:24][CH:25]1[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH2:26]1>C1(C)C=CC=CC=1>[C:25]1([CH2:24][N:1]2[CH2:6][CH2:5][CH:4]([N:7]([CH2:11][CH3:12])[C:8](=[O:10])[CH3:9])[CH2:3][CH2:2]2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:26]=1

Participants

4

Reactant 2

HCID 19761198N-Ethyl-N-4-piperidinylacetamideHCID 131717785HCID 131717785, compound

Product 1

HCID 19761220HCID 19761220, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.3 g of N-piperid-4-yl-N-ethylacetamide and 2.8 g of 1-methylbenzocyclobutene tosylate (prepared in accordance with the process described in J.A.C.S., (1975), 154, p. 347) are refluxed under nitrogen for 20 hours in 16 ml of toluene. After cooling, the reaction mixture is evaporated to dryness and taken up in diethyl ether. After extraction with N hydrochloric acid, the extract is rendered basic in the presence of diethyl ether and the organic phase is washed with water, dried over magnesium sulphate and evaporated in vacuo to yield N-[1-(benzocyclobuten-1-ylmethyl)-piperid-4-yl]-N-ethylacetamide. The corresponding hydrochloride is obtained in ethyl acetate in the presence of ethereal hydrogen chloride.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is evaporated to dryness
  3. extractionAfter extraction with N hydrochloric acid
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4b6e90e6618c4760bbd789708c1e98c4
Source dataset
uspto-grants-1993_02
Patent number
US05189045

Reaction notes

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