2-Bromobenzylamine hydrochloride → 2-Bromo-N-(tert-butoxycarbonyl)benzylamine

HRID 2247434Notes

Reaction equation

HRID 2247434 reaction equation
Cl.[Br:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[C:11](OC([O-])=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>O1CCCC1>[Br:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 27242022-Bromobenzylamine hydrochlorideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamineYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

15.0 g of 2-Bromobenzylamine hydrochloride was dissolved in 100 ml of tetrahydrofuran, and a solution of 13 g of t-butyl dicarbonate in tetrahydrofuran (25 ml) was added thereto. The mixture was stirred at room temperature for 1 hour, and then the solvent was evaporated. The residue was dissolved in ethyl acetate, and washed successively with 1N hydrochloric acid and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated, to give 16.0 g of the title compound.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed successively with 1N hydrochloric acid and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b11eb93fd399418695ca779846d3ebfa
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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