4-Chloropyridine → 3-(N-methyl-N-(4-pyridyl)amino)propanol

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:8][NH:9][CH2:10][CH2:11][CH2:12][OH:13]>>[CH3:8][N:9]([CH2:10][CH2:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 122884-Chloropyridine

HCID 101489863-(Methylamino)-1-propanol

Product 1

HCID 226250383-(N-methyl-N-(4-pyridyl)amino)propanolYield 2,560.8%

Procedure

Using a procedure analogous to that described for the starting material in Example 46, 4-chloropyridine (885 mg, 59 mmol) and 3-(methylamino)propanol (2.1 g, 0.23 mmol), (Tetrahedron Lett. 1994, 35, 1545-1548), were heated for 8 hours to give 3-(N-methyl-N-(4-pyridyl)amino)propanol (979 mg, 61%). 1H NMR Spectrum: (CDCl3; CD3COOD) 1.8-1.9(m, 2H); 3.16(s, 3H); 3.6-3.75(m, 4H) 6.8(br s, 2H); 8.30(d, 2H) MS-ESI: 166 [MH]+

Workup

temperaturewere heated for 8 hours

Sources & evidence

ORD record: ord-b595912240e34571be4f06299d2c4ab9
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258951B1

Reaction notes

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