Aniline → 6-(4-(3-(Phenylamino)propyl)phenoxy)nicotinamide

HRID 228171Notes

Reaction equation

HRID 228171 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[CH:16][CH2:17][CH2:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][N:25]=2)=[CH:21][CH:20]=1.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[OH-].[Na+]>ClCCCl>[C:36]1([NH:35][CH2:16][CH2:17][CH2:18][C:19]2[CH:34]=[CH:33][C:22]([O:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][N:25]=3)=[CH:21][CH:20]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 597301476-[4-(3-Oxo-propyl)-phenoxy]-nicotinamide

Product 1

HCID 444349476-(4-(3-(Phenylamino)propyl)phenoxy)nicotinamideYield 8.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Add sodium triacetoxyborohydride (0.1633 g, 0.7705 mmol) to a stirred solution of 6-[4-(3-oxo-propyl)-phenoxy]-nicotinamide (0.1341 g, 0.4962 mmol), aniline (0.047 mL, 0.5158 mmol), and 1,2-dichloroethane (7 mL). Stir the reaction for 18 h at room temperature under nitrogen. Pour the reaction mixture into 1 N sodium hydroxide (50 mL), extract with dichloromethane (3×50 mL), dry the dichloromethane extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 0.6% concentrated ammonium hydroxide/6% ethanol/chloroform to yield 0.0142 g (8%) of 6-[4-(3-phenylamino-propyl)-phenoxy]-nicotinamide: mass spectrum (ion spray): m/z=348.1 (M+1); 1H NMR (CDCl3): 8.58 (d, 1H), 8.16 (dd, 1H), 7.26-7.18 (m, 7H), 7.10-7.04 (m, 2H), 6.97-6.94 (m, 1H), 6.79-6.51 (m, 2H), 3.19 (t, 2H), 2.76 (t, 2H), 2.04-1.97 (m, 3H).

Workup

  1. customthe reaction for 18 h at room temperature under nitrogen
  2. extractionextract with dichloromethane (3×50 mL)
  3. dry with materialdry the dichloromethane
  4. filtrationfilter
  5. concentrationconcentrate on a rotary evaporator
  6. customto give the crude product
  7. customThe crude product is purified by flash chromatography on silica gel eluting with 0.6% concentrated ammonium hydroxide/6% ethanol/chloroform

Sources & evidence

ORD record
ord-522dc2a82f8c47bfadebf856f0ce484d
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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