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

HRID 267333Notes

Reaction equation

HRID 267333 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2fc4e0481e7a441385c39fb9456cf422
Source dataset
uspto-grants-1976_03
Patent number
US03941782

Reaction notes

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