3-Amino-1-propanol → HCID 178428733, compound

HRID 1369199Notes

Reaction equation

HRID 1369199 reaction equation
Cl.Cl[C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N+:4]=1[O-:10].[NH2:11][CH2:12][CH2:13][CH2:14][OH:15].C([O-])(O)=O.[Na+]>C(O)(CC)(C)C.C(Cl)Cl>[OH:15][CH2:14][CH2:13][CH2:12][NH:11][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N+:4]=1[O-:10]

Participants

6

Reactant 3

HCID 90863-Amino-1-propanolHCID 516892Sodium BicarbonateHCID 18518311HCID 18518311, compound

Product 1

HCID 178428733HCID 178428733, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of 2-chloro-4-methylpyridine-N-oxide hydrochloride (7.16 g, 39 mmole), 3-aminopropanol (6.01 g, 80 mmole), and NaHCO3 (16.8 g, 200 mmole) in tert-amyl alcohol (50 mL) was heated at reflux for 19 hr. The reaction mixture was diluted with CH2Cl2 (200 mL) and filtered, and the filtrate was concentrated on the rotavap. Recrystallization from CH2Cl2/Et2O gave the title compound (5.41 g, 75%) as a yellow solid: TLC (15% MeOH/CH2Cl2) Rf 0.44; 1H NMR (400, CDCl3) δ7.92 (d, J=6.7, 1 H), 7.28 (br t, 1 H), 6.43 (s, 1 H), 6.33 (dd, J=6.6, 2.1 Hz, 1 H), 3.73 (t, J=5.7 Hz, 2 H), 3.47 (q, H=6.3 Hz, 2 H), 2.29 (s, 3 H), 1.82-1.88 (m, 2 H); MS (ES) m/e 183 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 19 hr
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated on the rotavap
  5. customRecrystallization from CH2Cl2/Et2O

Sources & evidence

ORD record
ord-8c3940cef9b7449e8a3fe65aa6e3adc0
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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