Hydrochloric Acid → 3-amino-N,N-dimethylbenzylamine

HRID 914966

Reaction equation

HRID 914966 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[CH:5]=1.Cl.Cl[Sn]Cl>CO>[CH3:13][N:2]([CH2:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH2:10])[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 308050Dimethyl-(3-nitrobenzyl)-amine

Product 1

HCID 992943-amino-N,N-dimethylbenzylamineYield 49.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 11 (1.2 g, 6.67 mmol) in methanol (100 mL) were sequentially added conc. HCl (10 mL) and SnCl2 (5 g, 26.67 mmol). The reaction mixture was stirred at room temperature overnight before it was partitioned between water and EtOAc (200 mL each). The organic layer was separated and washed with water (150 mL), brine (150 mL) and dried over Na2SO4. The solids were filtered and the filtrate was concentrated on a rotavap to give 12 (500 mg).

Workup

  1. customwas partitioned between water and EtOAc (200 mL each)
  2. customThe organic layer was separated
  3. washwashed with water (150 mL), brine (150 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solids were filtered
  6. concentrationthe filtrate was concentrated on a rotavap

Sources & evidence

ORD record
ord-eec84e5c1d714d66918bd10e24a6ffeb
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Linked notes

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