Hydrochloric Acid → HCID 178481016, compound

HRID 979895Notes

Reaction equation

HRID 979895 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][N:12]([CH3:15])[C:11]2=[O:16])=[CH:6][CH:5]=1)([O-])=O.[ClH:17].CCOCC>C(O)(=O)C.C(O)(C)C.C(OCC)(=O)C.[Rh]>[ClH:17].[NH2:1][C@@H:4]1[CH2:5][CH2:6][C@H:7]([N:10]2[CH2:14][CH2:13][N:12]([CH3:15])[C:11]2=[O:16])[CH2:8][CH2:9]1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 137323581-Methyl-3-(4-nitrophenyl)imidazolidin-2-one

Product 1

HCID 178481016HCID 178481016, compound

Reagents, catalysts & solvents 4

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(p-nitrophenyl)-3-methyl-2-imidazolidinone (12.45 g) in 150 ml glacial acetic acid, to which is added 6 g of 5% rhodium on alumina, is hydrogenated at 50° and 45 lbs. pressure. The catalyst is filtered off and the filtrate concentrated under reduced pressure. Water (25 ml) is added to the residue which is basified by addition of 50% aqueous sodium hydroxide while the mixture is cooled in an ice bath. Extraction with methylene chloride (5×70 ml), drying over anhydrous sodium sulfate, filtering and concentrating under reduced pressure gives crude 1-(4-aminocyclohexyl)-3-methyl-2-imidazolidinone. The oil is converted to the hydrochloride salt by dissolving in 100 ml isopropanol and adding a saturated solution of hydrogen chloride gas in ethyl acetate. Ether (50 ml) is added and the salt crystallizes on cooling to room temperature. Mixture is cooled further in the refrigerator. The solid is filtered off and dried to give cis 1-(4-aminocyclohexyl)-3-methyl-2-imidazolidinone hydrochloride, m.p. 287°-298°.

Workup

  1. customis hydrogenated at 50°
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate concentrated under reduced pressure
  4. additionWater (25 ml) is added to the residue which
  5. additionis basified by addition of 50% aqueous sodium hydroxide while the mixture
  6. temperatureis cooled in an ice bath
  7. extractionExtraction with methylene chloride (5×70 ml)
  8. dry with materialdrying over anhydrous sodium sulfate
  9. filtrationfiltering
  10. concentrationconcentrating under reduced pressure
  11. customgives crude 1-(4-aminocyclohexyl)-3-methyl-2-imidazolidinone
  12. customthe salt crystallizes
  13. temperatureMixture is cooled further in the refrigerator
  14. filtrationThe solid is filtered off
  15. customdried

Sources & evidence

ORD record
ord-8e117068d46b4abaa014d5ec2dd8e19c
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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