Benzaldehyde → 2-[4-(2-Benzylaminoethyl)phenoxy]nicotinamide

HRID 228270Notes

Reaction equation

HRID 228270 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[N:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])=[CH:6][CH:5]=1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+]>CO>[CH2:20]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[N:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])=[CH:18][CH:19]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 597303512-[4-(2-Aminoethyl)phenoxy]nicotinamide

Product 1

HCID 444349332-[4-(2-Benzylaminoethyl)phenoxy]nicotinamideYield 1,107.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Take up 2-[4-(2-aminoethyl)phenoxy]nicotinamide (0.0555 g, 0.216 mmol) in methanol (2.1 mL). Add benzaldehyde (0.022 mL, 0.216 mmol) and 3 Å molecular sieves. Stir at room temperature overnight. Add NaBH4 (0.0082 g, 0.216 mmol) and stir for 6 hours before loading directly onto an SCX column. Wash the column with methanol then elute with 2.0 M NH3 in methanol. Purify by flash chromatography, eluting with 4% (2.0 M NH3 in methane) in dichloromethane to give the title compound (0.831 g, 79%): TOF MS ES+ 348.2 (M+H)+, HRMS calcd for C21H22N3O2 348.1712 (M+H)+, found 348.1721, time 0.35 min; TLC [silica gel 60 F254, 5% (2.0 M NH3 in methanol) in dichloromethane] Rf=0.20.

Workup

  1. washWash the column with methanol
  2. washthen elute with 2.0 M NH3 in methanol
  3. customPurify by flash chromatography
  4. washeluting with 4% (2.0 M NH3 in methane) in dichloromethane

Sources & evidence

ORD record
ord-2e5b2d7112f04cfcb3bcd96ef0cc979c
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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