Hydrochloric Acid → HCID 178481016, 화합물

HRID 979895노트

반응식

HRID 979895 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

HCID 178481016HCID 178481016, 화합물

시약·촉매·용매 4

HCID 23948Rhodium촉매HCID 176Acetic Acid용매HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-8e117068d46b4abaa014d5ec2dd8e19c
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04634713

반응 노트

불러오는 중…