Acetic Acid → 3-(Benzylamino-methyl)-benzoic acid methyl ester

HRID 418357

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH2:12])[CH:6]=1.CC(O)=O.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>ClC(Cl)C.CO>[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Suspended 3-aminomethyl-benzoic acid methyl ester hydrochloride (100 mg. 0.99 mmol) in 3 mL of dichloroethane in a microwave tube and added 100 uL of AcOH. To this was added benzaldehyde (0.10 mL, 1.00 mmol). The mixture was sealed and heated at 120° C. for 20 minutes resulting in a homogeneous solution. 2 mL of MeOH was added and the mixture was treated with NaBH4 (56.8 mg, 1.50 mmol) resulting in gas evolution. The mixture stirred for 19 h. The mixture was quenched with careful addition of 5% HCl resulting in a bi-phasic mixture. The aqueous phase was removed and treated with 50×2-200 Dowex acidic ion exchange resin. The product was liberated with 10% NH3 in MeOH and concentrated to give 197 mg of 3-(benzylamino-methyl)-benzoic acid methyl ester, partially contaminated with starting benzyl amine (15%).

Workup

customThe mixture was sealed
customresulting in a homogeneous solution
customresulting in gas evolution
customThe mixture was quenched with careful addition of 5% HCl resulting in a bi-phasic mixture
customThe aqueous phase was removed
additiontreated with 50×2-200 Dowex acidic ion exchange resin
concentrationconcentrated

Sources & evidence

ORD record: ord-1f7dce752bee41079aa1568231eb9191
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093266B2

Linked notes

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