Methyl chloroformate → HCID 3614573, compound

HRID 1901432Notes

Reaction equation

HRID 1901432 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl[C:14]([O:16][CH3:17])=[O:15].C(OCC)(=O)C>C1COCC1.O>[CH3:17][O:16][C:14]([NH:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:15]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 162593-Phenylpropylamine

Product 1

HCID 3614573HCID 3614573, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 3-phenyl-1-propylamine (19.6 g, mmol) in THF (50 mL) and water (50 mL) was adjusted to pH 9.0 with 2N NaOH. To the reaction was added methyl chloroformate (12.3 mL, 159 mmol) dropwise while the pH was maintained at 9.0 with 2N NaOH. After the reaction was stirred for an additional 30 minutes at room temperature, ethyl acetate (250 mL) was added. The organic layer was separated, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to give a clear oil of pure title compound (28 g, 100 percent yield):

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-556e6fd1f6ed4126a8251448d96013f5
Source dataset
uspto-grants-1996_11
Patent number
US05578574

Reaction notes

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