Pyridine → Methyl [2-(4-bromophenyl)-1-methylethyl]carbamate

HRID 2090340

Reaction equation

HRID 2090340 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH2:11])[CH3:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:19]([O:21][CH3:22])=[O:20]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([NH:11][C:19](=[O:20])[O:21][CH3:22])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 2056684-Bromo-alpha-methylbenzeneethanamine

Product 1

HCID 59402313Methyl [2-(4-bromophenyl)-1-methylethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromophenyl)propan-2-amine (0.5 g, 2 mmol) in methylene chloride (5 mL) was added pyridine (380 uL, 4.7 mmol) and methyl chloroformate (270 uL, 3.5 mmol, Aldrich, Cat. No. M35304). The reaction mixture was stirred at r.t. overnight, and concentrated under reduced pressure. The residue was dissolved in EtOAc, and washed with NaHCO3 aqueous solution, 1N HCl aqueous solution and brine. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatograph on a silica gel column using 25% Ethyl acetate in hexane to afford the desired compound. LCMS (M+H)+: m/z=272.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with NaHCO3 aqueous solution, 1N HCl aqueous solution and brine
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatograph on a silica gel column

Sources & evidence

ORD record
ord-e6a0159922a247c797a3839c9ef80c8a
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Linked notes

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