Potassium Carbonate → tert-butyl N-(3-bromopropyl)carbamate

HRID 1269145Notes

Reaction equation

HRID 1269145 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].[O:7](C(OC(C)(C)C)=O)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=O.C([O-])([O-])=O.[K+].[K+]>C(O)C>[Br:2][CH2:3][CH2:4][CH2:5][NH:6][C:8](=[O:7])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 787013-Bromopropylamine hydrobromideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 4460490tert-butyl N-(3-bromopropyl)carbamateYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-bromopropylamine hydrobromide (10.9 g, 49.8 mmol), BOC2O (11.4 g, 52.3 mmol) and K2CO3 (20.6 g, 149.4 mmol) in ethanol (100 ml) were stirred at room temperature overnight. The precipitated salts were removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water, followed by brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give 11.2 g (46.9 mmol, 94%) of the desired product: 1H NMR (400 MHz, CDCl3) δ 5.07 (br, 1H), 3.31 (t, 2H, J=6.6 Hz), 3.12 (apparent br q, 2H, J=6.0 Hz), 1.92 (quintet, 2H, J=6.6 Hz), 1.30 (s, 9H).

Workup

  1. customThe precipitated salts were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-488872bae77947bca0dc0df1f9cd159b
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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