Acetic Acid → HCID 58565161, compound

HRID 554596Notes

Reaction equation

HRID 554596 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH:12]=O)[CH:6]=1)[CH3:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CCO>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH2:12][NH:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 58565018HCID 58565018, compound

Product 1

HCID 58565161HCID 58565161, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromo-3-formyl-benzoic acid ethyl ester (3.3 g, 12.9 mmol) and benzylamine (2.1 mL, 19.3 mmol) were combined in EtOH (150 mL) with 4 Å molecular sieves. Sodium cyanoborohydride (1.21 g, 19.3 mmol) was added, followed by acetic acid (1.1 mL, 19.3 mmol), and the reaction was stirred at room temperature for 1 hour. Aqueous work-up provided 3-(benzylamino-methyl)-4-bromo-benzoic acid ethyl ester.

Sources & evidence

ORD record
ord-32786067136644f18febaa7a9f40b39f
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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