Phenethylamine → {3-[4-Bromo-2-(phenethylamino-methyl)-phenoxy]-phenyl}-acetic acid

HRID 1969015Notes

Reaction equation

HRID 1969015 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[C:4]([CH:19]=O)[CH:3]=1.[C:21]1([CH2:27][CH2:28][NH2:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[C:4]([CH2:19][NH:29][CH2:28][CH2:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 5003444Sodium cyanoborohydrideHCID 58237510[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid

Product 1

HCID 58288481{3-[4-Bromo-2-(phenethylamino-methyl)-phenoxy]-phenyl}-acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid (0.4 g, 1.23 mmol), 2-phenylethylamine (0.16 mL, 1.23 mmol), sodium cyanoborohydride (0.189 g, 3.0 mmol), and acetic acid (2 drops) were combined in CH2Cl2 and stirred at room temperature for 10 minutes. Aqueous work-up yielded the title compound.

Sources & evidence

ORD record
ord-e6b213778c234b7c931aca04f55476af
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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