Water → N-(2-pyridylmethyl)-5-bromopentanamide

HRID 1033245Notes

Reaction equation

HRID 1033245 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22].O>O1CCCC1>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][Br:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 5211735-Bromovaleryl chloride

Product 1

HCID 19025799N-(2-pyridylmethyl)-5-bromopentanamideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Part A. A solution of 2-(aminomethyl)pyridine (4.07 g, 37.6 mmol) and triethylamine (7.50 mL, 53.8 mmol) in tetrahydrofuran (100 mL) was cooled to 0° C., then treated with a solution of 5-bromovaleryl chloride (5.00 mL, 37.6 mmol) in tetrahydrofuran (20 mL) dropwise. After stirring for 12 hours, the mixture was poured into water (150 mL) and extracted with methylene chloride (2×150 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the oily product, N-(2-pyridylmethyl)-5-bromopentanamide (9.44 g, 34.8 mmol, 93%).

Workup

  1. extractionextracted with methylene chloride (2×150 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-4e0d3dc86c9c421eb2b38b113c703d8e
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

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