1-Chloroethyl chloroformate → HCID 66594394, compound

HRID 1091364Notes

Reaction equation

HRID 1091364 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=2[O:22][CH3:23])[CH2:9]1)C1C=CC=CC=1.[Cl:24]C(OC(Cl)C)=O>ClCCCl>[ClH:24].[C:20]([C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[C:14]([C@@H:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:19]=1)#[N:21]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 66594865HCID 66594865, compound

Product 1

HCID 66594394HCID 66594394, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (2S)-4-benzyl-2-(5-cyano-2-methoxyphenyl)-morpholine (10.8 g, 35.0 mmol) in 1,2-dichloroethane (80 ml) was added 1-chloroethyl chloroformate (5.73 ml, 52.5 mmol) at room temperature. Upon disappearance of the starting material, the reaction mixture was concentrated under reduced pressure. The residue was then dissolved in methanol (100 ml) and refluxed for 30 minutes. The solvents were removed in vacuo and the residue was filtered and washed with ethyl acetate to afford (2S)-2-(5-cyano-2-methoxyphenyl)-morpholine hydrochloride (8.08 g, 91%) as white solids.

Workup

  1. concentrationUpon disappearance of the starting material, the reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was then dissolved in methanol (100 ml)
  3. temperaturerefluxed for 30 minutes
  4. customThe solvents were removed in vacuo
  5. filtrationthe residue was filtered
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-4a02d33576ef4e4589740ee2e1744d70
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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