Acetic Acid → HCID 71811815, compound

HRID 2206870Notes

Reaction equation

HRID 2206870 reaction equation
[C:1]1([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[C:13](=O)[CH3:14])[CH2:5][CH2:4][CH2:3][CH:2]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]1([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[CH:13]([NH:19][CH:16]2[CH2:18][CH2:17]2)[CH3:14])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 89826215HCID 89826215, compound

Product 1

HCID 71811815HCID 71811815, compoundYield 132.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 510 mg (2.49 mmol) of 1-[2-(cyclopent-1-en-1-yl)-5-fluorophenyl]ethanone in 5 mL of methanol is added 0.5 g of 3 Å molecular sieves followed by addition of 285 mg (5 mmol) of cyclopropylamine and 375 mg (6.24 mmol) of acetic acid. The reaction mixture is stirred for 90 min at reflux. The reaction mixture is then cooled to 0° C. and 235 mg (3.74 mmol) of sodium cyanoborohydride are slowly added. The reaction mixture is further stirred for 2 hours at reflux. The cooled reaction mixture is filtered over a cake of diatomaceous earth and the cake is washed by ethyl acetate. The aqueous phase is extracted by ethyl acetate and the combined organic extracts are washed by a 1N aqueous solution of sodium hydroxide followed by a saturated aqueous solution of NaCl and dried over a ChemElut™ cartridge. Vacuum concentration yields 810 mg of crude N-{1-[2-(cyclopent-1-en-1-yl)-5-fluorophenyl]ethyl}cyclopropanamine as a brown oil used as such in the next step: (M+H)=246.

Workup

  1. temperatureat reflux
  2. stirringThe reaction mixture is further stirred for 2 hours
  3. temperatureat reflux
  4. customThe cooled reaction mixture
  5. filtrationis filtered over a cake of diatomaceous earth
  6. washthe cake is washed by ethyl acetate
  7. extractionThe aqueous phase is extracted by ethyl acetate
  8. washthe combined organic extracts are washed by a 1N aqueous solution of sodium hydroxide
  9. customdried over a ChemElut™ cartridge
  10. concentrationVacuum concentration

Sources & evidence

ORD record
ord-bcdb7803a36b4e7b8340658dfe7222d1
Source dataset
uspto-grants-2016_06
Patent number
US09374998B2

Reaction notes

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