Benzaldehyde → HCID 44434934, compound

HRID 130812Notes

Reaction equation

HRID 130812 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)=[CH:6][CH:5]=1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH3-]C#N.[Na+]>CO>[CH2:19]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)=[CH:17][CH:18]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59729993HCID 59729993, compound

Product 1

HCID 44434934HCID 44434934, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 6-[4-(2-aminoethyl)phenoxy]nicotinonitrile (2.09 g, 8.75 mmol) in methanol. Add 3 Å molecular sieves and benzaldehyde (0.89 mL, 8.75 mmol). Stir at room temperature for 18 hours. Add NaBH3CN (1.10 g). After the bubbling subsides, filter. Purify by flash chromatography, eluting with 3% (2.0 M NH3 in methanol) in dichloromethane to give the title compound: HRMS calcd for C22H20N3O 330.1620 (M+H)+, found 330.1620, time 0.39 min, MS TOF ES+ 330.2 (M+H)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=2.4 min, 100% purity.

Workup

  1. filtrationAfter the bubbling subsides, filter
  2. customPurify by flash chromatography
  3. washeluting with 3% (2.0 M NH3 in methanol) in dichloromethane

Sources & evidence

ORD record
ord-30702ce0d0cc48dd9ce4e192cf5af817
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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