Diisopropylethylamine → HCID 23577267, compound

HRID 1827251Notes

Reaction equation

HRID 1827251 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C>COCCO>[CH2:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([CH2:10][NH:9][C:2]2[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:12][CH2:13]1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27827912-Chloro-3-fluoropyridineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 23577267HCID 23577267, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 2-chloro-3-fluoropyridine (prepared in a manner similar to that described by W. J. Link, R. F. Borne and F. L. Setliff, J. Heterocyclic Chem. 4, 641–3, 1967) (131 mg 1 mmol), benzyl 4-(aminomethyl)piperidine-1-carboxylate (EXAMPLE 13, STEP 1) (248 mg, 1 mol) and diisopropylethylamine (129 mg, 1 mmol) were heated to reflux in 2-methoxyethanol for 2 days under nitrogen. The reaction mixture was concentrated, partitioned between ethyl acetate and water, the organic layer washed with brine, dried over anhydrous sodium sulfate and solvent evaporated to give the crude product purified by chromatography on silica. M.S. (M+1): 344.3

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washthe organic layer washed with brine
  4. dry with materialdried over anhydrous sodium sulfate and solvent
  5. customevaporated

Sources & evidence

ORD record
ord-dd7a303d0f304673af0107c1a82977d6
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

Loading…