Dimethylformamide → 882562-53-0

HRID 1880840Notes

Reaction equation

HRID 1880840 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:14][C:15]([NH:17][CH3:18])=[O:16].C[N:20](C=O)C>CCOC(C)=O>[NH2:20][CH:4]1[CH2:5][CH2:6][N:1]([CH2:14][C:15]([NH:17][CH3:18])=[O:16])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 667732-chloro-N-methylacetamide

Product 1

HCID 18071178882562-53-0

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2.0 g (10 mmoles) of piperidine, which as dissolved in DMF, anhydrous, 100 mL, was added 2.8 g (20 mmoles) K2CO3, and 1.2 g (11 mmoles) 2-chloro-N-methylacetamide. After stirring at 50° C. for overnight, the mixture was diluted with 500 mL of EtOAc, washed with brine (3×500 mL), dried over Na2SO4, and solvent was evaporated in vacuum. The resulting residue was treated with 50% TFA/DCM and was stirred at r.t. for 2 hrs, and solvent was evaporated in vacuum. The resulting mixture was purified by prep HPLC to give yellow oil, yield 1.5 g (88%). [M+H] calc'd for C8H17N3O, 172; found 172.

Workup

  1. washwashed with brine (3×500 mL)
  2. dry with materialdried over Na2SO4, and solvent
  3. customwas evaporated in vacuum
  4. additionThe resulting residue was treated with 50% TFA/DCM
  5. stirringwas stirred at r.t. for 2 hrs
  6. customsolvent was evaporated in vacuum
  7. customThe resulting mixture was purified by prep HPLC
  8. customto give yellow oil, yield 1.5 g (88%)

Sources & evidence

ORD record
ord-3e40c984a964466dabc4ef96422a13d3
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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