Diethylamine → Benzoic acid, 4-[(diethylaMino)Methyl]-, Methyl ester

HRID 131266Notes

Reaction equation

HRID 131266 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.C(Cl)(Cl)Cl.C(O)(=O)C>[CH2:13]([N:15]([CH2:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH2:16][CH3:17])[CH3:14]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 15294Methyl 4-FormylbenzoateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 12299003Benzoic acid, 4-[(diethylaMino)Methyl]-, Methyl esterYield 60%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of methyl 4-formylbenzoate (300 mg) in 1,2-dichloroethane (6 mL) is added diethylamine (113 μL), and thereto is added sodium triacetoxyborohydride (581 mg) and acetic acid (261 μL) under ice-cooling. The mixture is stirred at room temperature for 18 hours. The reaction mixture is diluted with chloroform (5 mL) and thereto is added a saturated sodium hydrogencarbonate solution (10 mL). After stirring, the organic layer is separated and concentrated. The resultant crude product is purified by column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=70:30→40:60) to give methyl 4-(diethylaminomethyl)benzoate (144 mg, yield; 60%) as an oil. MS (APCI) m/z: 222 [M+H]+

Workup

  1. temperaturecooling
  2. stirringAfter stirring
  3. customthe organic layer is separated
  4. concentrationconcentrated
  5. customThe resultant crude product is purified by column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=70:30→40:60)

Sources & evidence

ORD record
ord-c87a9031eef64c7988b1b0928497c4b8
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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