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

HRID 267333노트

반응식

HRID 267333 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][CH2:50][C:51](O)=[O:52])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>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:51](=[O:52])[CH2:50][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

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 215348Cyclopenta(c)(1)benzopyran-9-ol, 1,2,3,4-tetrahydro-4,4-dimethyl-7-(1,2-dimethylheptyl)-HCID 131720814-(Piperidin-1-yl)butanoic acid hydrochloride

생성물 1

HCID 681350854,4-Dimethyl-7-(3-methyl-2-octyl)-9-[4-(piperidino)-butyryloxy]-1,2,3,4-tetrahydrocyclopenta[c][1]benzopyran hydrochloride

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5.0 g. (14.6 mmoles) of 4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[ c][1]benzopyran, 3.14 g. (15.2 mmoles) of dicyclohexylcarbodiimide and 3.15 g. (15.2 mmoles) of γ-piperidinobutyric acid hydrochloride (m.p. 190°-192°), Cruickshank & Sheehan J. Am. Chem. Soc. 83, 2891 (1961), were combined with 250 ml. of methylene chloride and stirred for a total of 40 hours at room temperature. The insoluble by-product of dicyclohexylurea was separated by filtration and the methylene chloride was removed using a rotary evaporator. The brown residue was treated with approximately 75 ml. of benzene, and filtered to remove a small amount of insoluble material. The benzene was evaporated and the brown, viscous residue was triturated with about 200 ml. of ether to give 4.3 g. of crude product as a light brown solid, m.p. 174°-176°C. Recrystallization from benzene gave a total of 3.5 g. (45%) of product as colorless crystals, m.p. 174°-176°C. The infrared and nuclear magnetic resonance spectra were in agreement with the proposed structure.

후처리

  1. customThe insoluble by-product of dicyclohexylurea was separated by filtration
  2. customthe methylene chloride was removed
  3. customa rotary evaporator
  4. additionThe brown residue was treated with approximately 75 ml
  5. filtrationof benzene, and filtered
  6. customto remove a small amount of insoluble material
  7. customThe benzene was evaporated
  8. customthe brown, viscous residue was triturated with about 200 ml
  9. customof ether to give 4.3 g
  10. customRecrystallization from benzene
  11. customgave a total of 3.5 g

출처 및 근거

ORD 기록
ord-2fc4e0481e7a441385c39fb9456cf422
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03941782

반응 노트

불러오는 중…