Sulfuric acid magnesium salt (1:1) → [(6-Chloro(3-pyridyl)methyl][(4-methoxyphenyl)methyl]amino}ethan-1-ol

HRID 549218Notes

Reaction equation

HRID 549218 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11]O)=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=[O:25])C.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>ClCCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH:10]([OH:25])[CH3:11])[CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 153902972-[(6-Chloro-pyridin-3-ylmethyl)-amino]-ethanol

Product 1

HCID 86624864[(6-Chloro(3-pyridyl)methyl][(4-methoxyphenyl)methyl]amino}ethan-1-olYield 116.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

This compound was prepared in a manner analogous to that of Step A of Example 1, using 4.9 grams (0.026 mole) of 2-{[(6-chloro-3-pyridyl)methyl]amino}ethan-1-ol, 3.6 grams (0.026 mole) of 4-methoxybenzaldehyde, 8.3 grams (0.039 mole) of sodium triacetoxyborohydride and 5.8 grams (0.052 mole) of magnesium sulfate in 200 mL of 1,2-dichloroethane. The crude product was purified with column chromatography on silica gel. Elution was accomplished using 100% methylene chloride and 100% diethyl ether as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 9.3 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step A of Example 1
  2. customThe crude product was purified with column chromatography on silica gel
  3. washElution
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be6bb73c9c2743158025da84eb4c80ec
Source dataset
uspto-grants-2011_05
Patent number
US07943642B2

Reaction notes

Loading…