Diethyl Ether → HCID 86709917, compound

HRID 2179123Notes

Reaction equation

HRID 2179123 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](=O)([O-])[O-].[K+].[K+].[CH:16]1([NH2:20])[CH2:19][CH2:18][CH2:17]1.CCO[CH2:24][CH3:25]>O>[CH:16]1([N:20]([CH2:10][C:24]#[CH:25])[C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 75645Cyclobutylamine

Product 1

HCID 86709917HCID 86709917, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of benzoyl chloride (10.90 mL, 94.60 mmol) in ether (250 mL) and water (150 mL) was cooled over ice. Potassium carbonate (14.62 g, 105.78 mmol) was added followed by drop wise addition of cyclobutylamine (6.00 mL, 70.28 mmol). The ice was removed and the mixture stirred at 25° C. for 48 hours. DCM (350 mL) was added and the mixture washed with water (2×250 mL). The aqueous was back extracted with DCM (2×150 mL). The combined organic extracts were dried over MgSO4, filtered and evaporated to dryness under reduced vacuum to afford the crude N-(cyclobutyl)benzamide (12.14 g, 69.26 mmol, 98.6% yield) which was used directly in the next reaction.

Workup

  1. temperaturewas cooled over ice
  2. customThe ice was removed
  3. additionDCM (350 mL) was added
  4. washthe mixture washed with water (2×250 mL)
  5. extractionThe aqueous was back extracted with DCM (2×150 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness under reduced vacuum

Sources & evidence

ORD record
ord-b627a7d8fec542c8b7e283cff3f82da6
Source dataset
uspto-grants-2015_06
Patent number
US09067963B2

Reaction notes

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