Hydrochloric Acid → Methyl 3-(aminomethyl)benzoate

HRID 1717044Notes

Reaction equation

HRID 1717044 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9](=[O:35])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH:17]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH:11]=1.O.Cl>CN(C=O)C>[CH3:7][O:8][C:9](=[O:35])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH2:17])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8082PiperidineHCID 58482930HCID 58482930, compound

Product 1

HCID 2794826Methyl 3-(aminomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 20% solution of piperidine in DMF (5 ml) was added to 3-[(9H-Fluoren-9-ylmethoxycarbonylamino)-methyl]-benzoic acid methyl ester (193 mg, 0.5 mmol) and the reaction was stirred at room temperature for 30 min. Water (10 ml) was added to the crude reaction mixture, followed by 1M HCl (10 ml). The aqueous layer was washed with EtOAc (3×10 ml) then basified to pH 9 with saturated NaHCO3. The basic layer was extracted with EtOAc (3×10 ml) and the aqueous layer was evaporated down to a small volume, then further extracted with EtOAc (5×10 ml). The combined organic layers were dried (MgSO4), filtered and the solvent evaporated in vacuo to give the title compound.

Workup

  1. customreaction mixture
  2. washThe aqueous layer was washed with EtOAc (3×10 ml)
  3. extractionThe basic layer was extracted with EtOAc (3×10 ml)
  4. customthe aqueous layer was evaporated down to a small volume
  5. extractionfurther extracted with EtOAc (5×10 ml)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-b3957ca15881429698e06cc87c9f4615
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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