4-Chlorobenzaldehyde → [(6-Chloro(3-pyridyl)methyl][(4-chlorophenyl)methyl]amino}ethan-1-ol

HRID 549226Notes

Reaction equation

HRID 549226 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.[Cl:13][C:14]1[CH:21]=[CH:20]C(C=O)=[CH:16][CH:15]=1.[C:22](O[BH-](OC(=O)C)OC(=O)C)(=[O:24])[CH3:23].[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:22]([OH:24])[CH3:23])[CH2:10][C:11]2[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5049666Sodium triacetoxyborohydrideHCID 153902972-[(6-Chloro-pyridin-3-ylmethyl)-amino]-ethanol

Product 1

HCID 86624869[(6-Chloro(3-pyridyl)methyl][(4-chlorophenyl)methyl]amino}ethan-1-olYield 94.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

This compound was prepared in a manner analogous to that set forth in Step A of Example 1, using 5.0 grams (0.0268 mole) of 2-{[(6-chloro-3-pyridyl)methyl]amino}ethan-1-ol (prepared in Step A of Example 1), 3.8 grams (0.0268 mole) of 4-chlorobenzaldehyde, 8.5 grams (0.040 mole) of sodium triacetoxyborohydride and 6.5 grams (0.053 mole) of magnesium sulfate in 100 mL of 1,2-dichloroethane. The crude product was purified with column chromatography on silica gel. Elution was accomplished using 2% methanol in methylene chloride as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 7.9 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 set forth in 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-197d51f7ec744451b4973628c37b351c
Source dataset
uspto-grants-2011_05
Patent number
US07943642B2

Reaction notes

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