Chloroacetyl chloride → 2-chloro-N-{4-[(2S)-4-((1R)-1-phenylethyl)morpholin-2-yl]phenyl}acetamide

HRID 424442Notes

Reaction equation

HRID 424442 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:29][CH2:30][C:31](Cl)=[O:32]>O1CCCC1>[Cl:29][CH2:30][C:31]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C@@H:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:15])[CH2:9]2)=[CH:6][CH:7]=1)=[O:32]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66594463HCID 66594463, compound

Product 1

HCID 665946402-chloro-N-{4-[(2S)-4-((1R)-1-phenylethyl)morpholin-2-yl]phenyl}acetamideYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-2-(4-aminophenyl)-4-((1R)-1-phenylethyl)morpholine (2.93 g, 10 mmol) and triethylamine (3.0 g, 30 mmol) in tetrahydrofuran (50 ml) was added chloroacetyl chloride (2.26 g, 20 mmol). The mixture was stirred at room temperature for 2 hours and partitioned between water and chloroform. The organic extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the precipitated crystals were collected by filtration, washed with isopropyl ether to give 2-chloro-N-{4-[(2S)-4-((1R)-1-phenylethyl)morpholin-2-yl]phenyl}acetamide (3.5 g, 97%) as yellow crystals.

Workup

  1. custompartitioned between water and chloroform
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. filtrationthe precipitated crystals were collected by filtration
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-fb5ae656b9fa4eb8b9c9f480327705d4
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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