Sodium Hydroxide → HCID 21071685, compound

HRID 1371932Notes

Reaction equation

HRID 1371932 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:28](I)[CH2:29][CH3:30]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:3]([O:7][C:8]([N:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][CH3:30])[CH:22]=1)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 21071684HCID 21071684, compound

Product 1

HCID 21071685HCID 21071685, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Add a solution of 50% sodium hydroxide in water (0.8 mL) to a solution of N-t-butoxycarbonyl-N-2-(3-chlorophenyl)ethyl-3-hydroxybenzylamine (46.7 mg, 0.129 mmol), n-propyl iodide (0.17 gm. 1.00 mmol), and tetrabutylammonium bromide (18 mg, 0.057 mmol) in toluene (1 mL). Stir the mixture at 1200 rpm and heat at 50–54° C. After 64.5 hour pour the mixture into 5 mL of water, separate the phases and extract the aqueous phase twice with dichloromethane. Combine the organic phases and wash with saturated sodium bicarbonate solution, and then saturated brine, dry (MgSO4), and concentrate to give a residue. Chromatograph the residue on silica gel to give the title compound: MS (ES+): m/e (M+1) 404. TLC (20% EtOAc in hexanes, Rf 0.54).

Workup

  1. temperatureheat at 50–54° C
  2. customseparate the phases
  3. extractionextract the aqueous phase twice with dichloromethane
  4. washwash with saturated sodium bicarbonate solution
  5. dry with materialsaturated brine, dry (MgSO4)
  6. concentrationconcentrate
  7. customto give a residue

Sources & evidence

ORD record
ord-7e4083d539b14a81a13f6392977f9d7e
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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