Tributylamine → N-(5-Bromo-pyridin-3-yl)-3-dimethylamino-propionamide

HRID 1878616Notes

Reaction equation

HRID 1878616 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.Cl.[CH3:10][N:11]([CH3:17])[CH2:12][CH2:13][C:14](O)=[O:15].C(N(CCCC)CCCC)CCC.[I-].ClC1C=CC=C[N+]=1C>C(Cl)Cl>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:14](=[O:15])[CH2:13][CH2:12][N:11]([CH3:17])[CH3:10])[CH:3]=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 8176813-Amino-5-bromopyridineHCID 115863273-(Dimethylamino)propanoic acid hydrochloride

Product 1

HCID 68763057N-(5-Bromo-pyridin-3-yl)-3-dimethylamino-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-amino-5-bromopyridine (Sigma-Aldrich, St. Louis, USA) (1 eq, 11.2 mmol, 2.00 g) and 3-dimethylaminopropionic acid hydrochloride (ABCR GmbH & Co. KG, Karlsruhe, Germany) (1 eq, 11.2 mmol, 1.74 g) in DCM (50 ml), tributylamine (3.6 eq, 40.4 mmol, 9.8 ml) and 2-chloro-1-methylpyridinium iodide (1.2 eq, 13.5 mmol, 3.54 g) are added. The resulting mixture is heated at 50° C. for 4 h, then the solvents are removed in vacuo, aqueous NaOH solution (1 M) is added, and the mixture is extracted with DCM. The organic layer is dried with MgSO4, filtered, and the solvent is removed in vacuo. Purification by column chromatography (DCM/MeOH) yields the title compound; [M+H]+=273.

Workup

  1. customthe solvents are removed in vacuo, aqueous NaOH solution (1 M)
  2. additionis added
  3. extractionthe mixture is extracted with DCM
  4. dry with materialThe organic layer is dried with MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customPurification by column chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-3d2afb53c695440d9e8d8c8949714e63
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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