N-Methylbenzylamine → HCID 22318810, compound

HRID 481108Notes

Reaction equation

HRID 481108 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]1[C:9]([CH:10]=O)=[CH:8][CH:7]=[CH:6][N:5]=1.[CH2:14]([NH:21][CH3:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C.O>[CH2:14]([N:21]([CH2:10][C:9]1[C:4]([CH:3]([O:12][CH3:13])[O:2][CH3:1])=[N:5][CH:6]=[CH:7][CH:8]=1)[CH3:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7669N-MethylbenzylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 22318798HCID 22318798, compound

Product 1

HCID 22318810HCID 22318810, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of 2.0 g (11 mmol) of 2-dimethoxymethyl-pyridin-3-carbaldehyde and 1.6 mL (12 mmol) of N-benzyl methyl amine in 30 mL of dichloroethane is added 4.7 g (22 mmol) of sodium triacetoxyborohydride. The reaction is stirred for 18 hours at room temperature. To this mixture is added 20 mL of water. After 1 hour of stirring the pH of the reaction mixture is adjusted to 8.0 with 1N NaOH. The organic layer is separated from the water layer, dried and evaporated to yield 1.9 grams of benzyl-(2-dimethoxymethyl-pyridin-3-ylmethyl)-methyl-amine. 1H NMR (CDCl3) δ8.5 (d, 1H), 7.9 (d, 1H), 7.3 (m, 6H), 5.6 (s, 1H), 3.7 (s, 2H), 3.5 (s, 2H), 3.3 (s, 6H) 2.1 (s, 3H). Mass spectrum: m/e=287.8 (p+1). TLC (1/1 ethyl acetate/hexanes) Rf=0.2.

Workup

  1. stirringAfter 1 hour of stirring the pH of the reaction mixture
  2. customThe organic layer is separated from the water layer
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-e6a2bba7f1aa4dbbac3dcf889277c11c
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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