Tert-Butylamine → HCID 57957417, compound

HRID 1392909Notes

Reaction equation

HRID 1392909 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[C:10]([NH2:14])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:10]([NH:14][CH2:8][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 57957417HCID 57957417, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (537 mg, 3.31 mmole) in 7 mL of dry acetonitrile is 0.7 mL (6.62 mmol) of tert-butylamine followed by 457 mg (3.31 mmol) of potassium carbonate. The reaction is heated at 80° C. for 12 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 387 mg (59% yield) of tert-Butyl-(6-chloro-pyridin-3-ylmethyl)-amine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.16 (s, 9H), 1.60–1.80 (brs, 1H0, 3.72 (s, 2H), 7.26 (d, 1H, J=8.3 Hz), 7.71 (dd, 1H, J=8.3 and 2.5 Hz), 8.33 (d, 1H, J=2.0 Hz); MS 199.2 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is quenched with 5 mL of water
  3. extractionextracted three-times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customConcentration of the solvent provided an oil which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-8a3468ad507c4ae1b05f42545d9eeb0b
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

Loading…