N-Methylpiperidine → HCID 70256050, compound

HRID 1585055Notes

Reaction equation

HRID 1585055 reaction equation
CN1CCCCC1.ClC(OCC(C)C)=O.[CH:16]([O:19][C:20]([NH:22][C:23](=[CH:27][CH3:28])[C:24]([OH:26])=O)=[O:21])([CH3:18])[CH3:17].[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([NH2:39])[CH3:38])=[CH:33][CH:32]=1>ClCCl>[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([NH:39][C:24](=[O:26])[C:23]([NH:22][C:20]([O:19][CH:16]([CH3:17])[CH3:18])=[O:21])=[CH:27][CH3:28])[CH3:38])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 2381811-(4-Methoxyphenyl)ethanamineHCID 53885343HCID 53885343, compound

Product 1

HCID 70256050HCID 70256050, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At -20° C., 0.5 g (0.005 mol) of N-methylpiperidine and then, dropwise with stirring at -20° C., 0.7 g (0.005 mol) of isobutyl chloroformate are added to 1.0 g (0.005 mol) of 2-(i-propoxycarbonylamino)-but-2-enoic acid in 10 ml of dichloromethane. After the addition is complete, stirring is continued at -20° C. for a further 10 minutes, and 0.75 g (0.005 mol) of 1-(4-methoxyphenyl)-ethylamine are added, the temperature being kept below -15° C. Stirring is then continued for a further 2 hours at -15° C. and for 15 hours at room temperature, the precipitated solid is filtered off and washed with dichloromethane, the filtrate is concentrated under reduced pressure, the residue is taken up in water and extracted repeatedly with ethyl acetate, the combined organic phases are washed with aqueous sodium bicarbonate solution and water and dried over sodium sulphate, and the solvent is removed under reduced pressure. 0.8 g (47% of theory) of N-[1-(4-methoxyphenyl)-ethyl]-2-(i-propoxycarbonylamino)-but-2-enoic acid amide are obtained as a colourless oil. 1H-NMR (CDCl3, TMS), δ (ppm): 1.25 (m, 6H), 1.50 (d, 3H); 1.74 (d, 3H); 3.79 (s, 3H).

Workup

  1. additionAfter the addition
  2. custombeing kept below -15° C
  3. stirringStirring
  4. waitis then continued for a further 2 hours at -15° C. and for 15 hours at room temperature
  5. filtrationthe precipitated solid is filtered off
  6. washwashed with dichloromethane
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. extractionextracted repeatedly with ethyl acetate
  9. washthe combined organic phases are washed with aqueous sodium bicarbonate solution and water
  10. dry with materialdried over sodium sulphate
  11. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-1c657087e87242b0bc16d133b65273b1
Source dataset
uspto-grants-1999_08
Patent number
US05935979

Reaction notes

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