Diisopropylethylamine → N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide

HRID 30805

Reaction equation

HRID 30805 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8](Cl)=[O:9])[CH2:4][CH2:3]1.[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:8]([CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:9])[CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4365031-Methylpiperidine-4-carbonyl chlorideHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 69008397N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A flask was flame dried and placed under a nitrogen atmosphere. 1-methylpiperidine-4-carbonyl chloride (1 eq) in anhydrous methylene chloride was added to the flask and brought to 0° C. To this was added the solution containing 4-chloropyridin-2-amine (1 eq), and diisopropylethylamine (5 eq) in anhydrous methylene chloride, which was stirred for 1 hour at 0° C. Reaction concentrated and partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to give the crude product. Purification on silica gel, 10% methanol in methylene chloride to yield N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide as a slightly yellow crystal solid. HPLC=2.39 min; MS: MH+=254.

Workup

  1. temperatureA flask was flame
  2. customdried
  3. custombrought to 0° C
  4. additionTo this was added the solution
  5. customReaction
  6. concentrationconcentrated
  7. custompartitioned between water and ethyl acetate
  8. customThe organic layer was separated
  9. washwashed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customto give the crude product
  13. customPurification on silica gel, 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-09769fb5fb4e43ffa1082f09d673b2a1
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Linked notes

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