1-Chloroethyl chloroformate → 4-((S)-Morpholin-2-YL)benzonitrile hcl

HRID 2045905Notes

Reaction equation

HRID 2045905 reaction equation
C1([C@H]([N:9]2[CH2:14][CH2:13][O:12][C@@H:11]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)[CH2:10]2)C)C=CC=CC=1.[Cl:23]C(OC(Cl)C)=O>ClCCCl>[ClH:23].[NH:9]1[CH2:14][CH2:13][O:12][C@@H:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 509925234-((S)-4-((R)-1-Phenylethyl)morpholin-2-yl)benzonitrile2×

Product 1

HCID 668608264-((S)-Morpholin-2-YL)benzonitrile hclYield 79%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-((2S)-4-((1R)-1-phenylethyl)morpholin-2-yl)benzonitrile (intermediate 9, 45.7 g, 156 mmol) in 1,2-dichloroethane (312 ml) was added 1-chloroethyl chloroformate (66.9 g, 468 mmol) at room temperature. After a reflux for 6 hours, the solution was concentrated under reduced pressure. The residue was dissolved in methanol (312 ml) and the solution was refluxed for 2 hours. After removal of the solvent under reduced pressure, the crude product was washed with acetone and dried under reduced pressure to afford 4-((2S)-morpholin-2-yl)benzonitrile hydrochloride (intermediate 10, 27.6 g, 79%).

Workup

  1. temperatureAfter a reflux for 6 hours
  2. concentrationthe solution was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (312 ml)
  4. temperaturethe solution was refluxed for 2 hours
  5. customAfter removal of the solvent under reduced pressure
  6. washthe crude product was washed with acetone
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-f9862db5897e4a319c903ccb5f93ae08
Source dataset
uspto-grants-2013_11
Patent number
US08592417B2

Reaction notes

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