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1,2-Dichloroethane → 2(S)-(4-Chloro-phenyl)-3(S)-ethyl-1-morpholin-4-yl-pent-4-en-1-one

HRID 733318
Notes
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Reaction equation

HRID 733318 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([C@H:18]([CH2:21][CH3:22])[CH:19]=[CH2:20])[C:15](O)=[O:16])=[CH:10][CH:9]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(Cl)CCl>CN(C=O)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14]([C@@H:18]([CH2:21][CH3:22])[CH:19]=[CH2:20])[C:15]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:16])=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 578390822(S)-(4-Chloro-phenyl)-3(R)-ethyl-pent-4-enoic acid

Product 1

HCID 685746972(S)-(4-Chloro-phenyl)-3(S)-ethyl-1-morpholin-4-yl-pent-4-en-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Morpholine (0.107 ml, 1.23 mmol) and the intermediate I2 (239 mg, 1.12 mmol) were dissolved in 5 ml of DMF and cooled in an ice-bath. HOBT (188 mg, 1.23 mmol), triethylamine (0.309 ml, 2.24 mmol) and EDC (214 mg, 1.12 mmol) were added successively. The ice-bath was removed and stirring continued over night. The mixture was evaporated, redissolved in diethyl ether and extracted with 2N-HCl (twice), 5% sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated to give a pale yellow oil. Yield (crude): 320 mg (93%).

Workup

  1. temperaturecooled in an ice-bath
  2. customThe ice-bath was removed
  3. waitcontinued over night
  4. customThe mixture was evaporated
  5. dissolutionredissolved in diethyl ether
  6. extractionextracted with 2N-HCl (twice), 5% sodium bicarbonate and brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customevaporated
  9. customto give a pale yellow oil
  10. customYield (crude)

Sources & evidence

ORD record
ord-e078812d410745eab19af42f00c64ab9
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07589091B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes