Acetone → S 38093-2

HRID 1183803Notes

Reaction equation

HRID 1183803 reaction equation
[CH2:1]1[C@H:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[CH2:3][N:2]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][CH:14]=1.CC(C)=O.[ClH:26]>O>[ClH:26].[CH2:1]1[C@H:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[CH2:3][N:2]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH2:19])=[O:18])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 709411121403835-45-9

Product 1

HCID 70945946S 38093-2Yield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

16.49 kg of 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1H)-yl]propoxy}benzamide, 16.36 kg of acetone, 6.76 kg of concentrated aqueous hydrochloric acid and 18.96 kg of water are introduced into a reactor. The mixture is stirred and heated at 50° C. for 1 hour. The mixture is then filtered in the hot state into a second reactor containing 57.67 kg of acetone and 1.65 kg of water. The mixture is then brought to reflux and 73.32 kg of acetone are added. Reflux is maintained for 10 minutes and then cooling to 0° C. is carried out. The product is filtered off and the solid obtained is washed with acetone. The product is obtained in the form of a powder in a yield of 85% and with a chemical purity greater than 99%.

Workup

  1. filtrationThe mixture is then filtered in the hot state into a second reactor
  2. additioncontaining 57.67 kg of acetone and 1.65 kg of water
  3. temperatureto reflux
  4. addition73.32 kg of acetone are added
  5. temperatureReflux
  6. temperatureis maintained for 10 minutes
  7. temperaturecooling to 0° C.
  8. filtrationThe product is filtered off
  9. customthe solid obtained
  10. washis washed with acetone
  11. customThe product is obtained in the form of a powder in a yield of 85% and with a chemical purity greater than 99%

Sources & evidence

ORD record
ord-52b2484f01e34f7e9694cafedb88bb4c
Source dataset
uspto-grants-2014_03
Patent number
US08664408B2

Reaction notes

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