Water → HCID 86682373, compound

HRID 2371030Notes

Reaction equation

HRID 2371030 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][O:6][CH:5]([C:10]3([NH2:13])[CH2:12][CH2:11]3)[C:4]=2[CH:3]=[CH:2]1.CCN([CH2:19][CH3:20])CC.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23].O.[CH2:28](Cl)Cl>>[S:1]1[C:9]2[CH2:8][CH2:7][O:6][CH:5]([C:10]3([NH:13][C:22](=[O:23])[O:24][CH2:25][CH3:26])[CH2:12][CH2:11][CH2:20][CH2:19][CH2:28]3)[C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 53238286HCID 53238286, compound

Product 1

HCID 86682373HCID 86682373, compoundYield 83%

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(6,7-dihydro-4H-thieno[3,2-c]pyran-4-yl)-cyclopropanamine (1 g, 5.1 mmol) and Et3N (0.8 g, 7.5 mmol) in dry DCM (20 mL) at 0° C. was added ethyl chloroformate (0.8 g, 7.5 mmol) dropwise. After stirring at 0° C. for 4 h, water (20 mL) was added to quench the reaction. The mixture was extracted with DCM (3×50 mL) and the organic extract was dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (1.1 g, 83%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with DCM (3×50 mL)
  4. extractionthe organic extract
  5. dry with materialwas dried over anhydrous Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-663e162ecbbe41a2b66c2225e1fdcc51
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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