Triethylamine → 4-Dimethylamino-N-(4-hydroxymethylbenzyl)benzamide

HRID 1727257Notes

Reaction equation

HRID 1727257 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[NH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][OH:44])=[CH:39][CH:38]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:12][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([CH2:43][OH:44])=[CH:39][CH:38]=2)=[O:9])=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 120924-(Dimethylamino)benzoic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 516892Sodium BicarbonateHCID 6496943[4-(Aminomethyl)phenyl]methanol

Product 1

HCID 114489864-Dimethylamino-N-(4-hydroxymethylbenzyl)benzamideYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(dimethylamino)benzoic acid (915 mg, 5.54 mmol) and triethylamine (772 μL, 5.54 mmol) in CH2Cl2 (25 mL) at 0° C. was added BOP-Cl (1.50 g, 6.09 mmol), and the mixture was stirred at room temperature for 20 minutes. To the reaction mixture was added (4-aminomethylphenyl)methanol (760 mg, 5.54 mmol) and triethylamine (1.54 mL, 11.08 mmol), and the mixture was stirred at room temperature overnight. To the reaction mixture was added a 50% aqueous NaHCO3 solution (50 mL), and the mixture was extracted with 5% MeOH in CHCl3 (100 mL×1, 40 mL×2). The organic layer was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by MPLC on silica gel (2% MeOH in CHCl3) to afford the titled compound (1.04 g, 66%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with 5% MeOH in CHCl3 (100 mL×1, 40 mL×2)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by MPLC on silica gel (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-f92a32e7765b476c9bd432db557a05dd
Source dataset
uspto-grants-2009_02
Patent number
US07495022B2

Reaction notes

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