Piperidine → HCID 24831098, compound

HRID 639307Notes

Reaction equation

HRID 639307 reaction equation
[CH:1]1([CH2:6][O:7][C:8]2[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[N:10][C:9]=2[N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC(N(C)C)=C(C)C.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(OCC)(=O)C>ClCCl>[CH:1]1([CH2:6][O:7][C:8]2[N:13]=[C:12]([C:14]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:16])[CH:11]=[N:10][C:9]=2[N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 68566019HCID 68566019, compound

Product 1

HCID 24831098HCID 24831098, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.0874 g (0.0003 mol) 6-cyclopentylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid in 1.0 mL dichloromethane was added 0.047 g (0.00035 mol)(1-chloro-N,N,2-trimethyl-1-propenylamine and the mixture was stirred at room temperature for 45 min. To the resulting solution was added 0.0683 g (0.0008 mol) piperidine and the mixture was stirred at room temperature for 2 h. The reaction mixture was partitioned between 10% citric acid and dichloromethane. The phases were separated and the organic phase was washed with water and brine, dried over sodium sulfate, evaporated and the residue was purified by chromatography on silica gel with dichloromethane:ethyl acetate=1:1 to yield 0.064 g (0.00018 mol) of the title compound as beige crystals melting at 61-62° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. customThe reaction mixture was partitioned between 10% citric acid and dichloromethane
  3. customThe phases were separated
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customthe residue was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-60614b14d2c64a9d8d709453c5a398bd
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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