Triethylamine → HCID 57485791, compound

HRID 597989Notes

Reaction equation

HRID 597989 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C(N(CC)CC)C.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>ClCCl>[CH:1]1([CH2:7][NH:8][C:17](=[O:18])[O:19][CH2:20][CH3:21])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 135126212555-10-4

Product 1

HCID 57485791HCID 57485791, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclohex-3-enylmethylamine (10 g, 90 mmol) was dissolved in 200 mL of dichloromethane and cooled in an ice bath. Triethylamine (16.8 mL, 120 mmol) was added, followed by drop-wise addition of ethyl chloroformate (10.9 g, 0.100 mol). The mixture was stirred overnight at ambient temperature, then washed with water, dilute HCl, dilute aqueous sodium hydroxide, and brine (50 mL each). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the crude carbamate (14 g, 85%).

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with water, dilute HCl, dilute aqueous sodium hydroxide, and brine (50 mL each)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2cd830a23c3d469f82776afc7936babe
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

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