Hydrochloric Acid → 4,4-Dimethyl-7-(3-methyl-2-octyl)-9-[3-(piperidino)-propionyloxy]-1,2,3,4-tetrahydrocyclopenta[c][1]-benzopyran hydrochloride

HRID 267334

반응식

HRID 267334 반응식
[CH3:1][C:2]1([CH3:25])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:24])=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[ClH:41].[N:42]1([CH2:48][CH2:49][C:50](O)=[O:51])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1.Cl>CCOCC.C(Cl)Cl>[ClH:41].[CH3:25][C:2]1([CH3:1])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:24][C:50](=[O:51])[CH2:49][CH2:48][N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 215348Cyclopenta(c)(1)benzopyran-9-ol, 1,2,3,4-tetrahydro-4,4-dimethyl-7-(1,2-dimethylheptyl)-HCID 131319213-(Piperidin-1-yl)propanoic acid hydrochloride

생성물 1

HCID 681275274,4-Dimethyl-7-(3-methyl-2-octyl)-9-[3-(piperidino)-propionyloxy]-1,2,3,4-tetrahydrocyclopenta[c][1]-benzopyran hydrochloride

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

2.8 g. (8.2 mmoles) of 4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[ c][1]benzopyran, 1.77 g. (8.6 mmoles) of dicyclohexylcarbodiimide and 1.65 g. (8.5 mmoles) of β-piperidinopropionic acid hydrochloride (m.p. 216°-220°C., J. Am. Chem. Soc. 73, 3168 (1951) were combined with 125 ml. of methylene chloride and stirred at room temperature for about 20 hours. The reaction mixture was filtered and the methylene chloride removed using a rotary evaporator. The residue was treated with benzene and filtered to remove a small quantity of insoluble material. The benzene was evaporated and the dark, viscous residue was chromatographed using 100 g. of 60-100 mesh activated magnesium silicate (Florisil) and methanol/chloroform graded solvent mixtures. Chromatography gave a small quantity of orange oil which was dissolved in ether and treated with a solution of ethereal HCl. The desired compound appeared as white crystals which were filtered and washed with additional ether. The colorless crystals (86 mg., m.p. 106°-107°C.) were pure by thin layer chromatography (10% MeOH/CHCl3) and the nuclear magnetic resonance and infrared spectra were in agreement with the proposed structure.

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe methylene chloride removed
  3. customa rotary evaporator
  4. additionThe residue was treated with benzene
  5. filtrationfiltered
  6. customto remove a small quantity of insoluble material
  7. customThe benzene was evaporated
  8. customthe dark, viscous residue was chromatographed
  9. customChromatography gave a small quantity of orange oil which

출처 및 근거

ORD 기록
ord-9c80297a6cb9413bbfa211643898bf99
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03941782

연결된 노트

불러오는 중…