4-Methoxybenzylamine → HCID 89600014, compound

HRID 2277625Notes

Reaction equation

HRID 2277625 reaction equation
CO[C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH2:11]Br.[CH2:14]([NH2:23])[C:15]1[CH:22]=[CH:21][C:18]([O:19][CH3:20])=[CH:17][CH:16]=1>C1COCC1>[F:10][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[C:3](=[O:13])[N:23]([CH2:14][C:15]1[CH:22]=[CH:21][C:18]([O:19][CH3:20])=[CH:17][CH:16]=1)[CH2:11]2

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 18323864Methyl 2-(bromomethyl)-4-fluorobenzoate

Product 1

HCID 89600014HCID 89600014, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-bromomethyl-4-fluoro-benzoic acid methyl ester (17 g, 68.8 mmol) in THF (200 mL) was added PMBNH2 (23.6 g, 172 mmol) at 0° C. After stirring at room temperature for 16 hours, the reaction mixture was concentrated in vacuo to give a crude product which was then purified by column chromatography to give the title compound (13 g, yield 69%) as a solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto give a crude product which
  3. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-d8426ee9f4b04d828ee845957fe5d845
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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