Dicyclohexylcarbodiimide → HCID 68122140, compound

HRID 2398890Notes

Reaction equation

HRID 2398890 reaction equation
[CH3:1][C:2]1([CH3:28])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:27])=[CH:12][C:13]([C:15]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH3:19])[CH2:16][CH2:17][CH3:18])=[CH:14][C:4]=2[O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[ClH:44].[N:45]1([CH2:51][CH2:52][CH2:53][C:54](O)=[O:55])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>C(Cl)Cl>[ClH:44].[CH3:28][C:2]1([CH3:1])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:27][C:54](=[O:55])[CH2:53][CH2:52][CH2:51][N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)=[CH:12][C:13]([C:15]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH3:19])[CH2:16][CH2:17][CH3:18])=[CH:14][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 131720814-(Piperidin-1-yl)butanoic acid hydrochlorideHCID 54468075HCID 54468075, compound

Product 1

HCID 68122140HCID 68122140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g. (14.6 mmoles) of 4,4-dimethyl-9-hydroxy-7-(4-fluorophenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta [c][1]benzopyran, prepared according to the method of Example 50, 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), are combined with 250 ml. of methylene chloride and stirred for a total of 40 hours at room temperature. The insoluble by-product of dicyclohexylurea is separated by filtration and the methylene chloride is removed using a rotary evaporator. The brown residue is treated with approximately 75 ml. of benzene, and filtered to remove a small amount of insoluble material. The benzene is evaporated and the viscous residue is triturated with about 200 ml. of ether to give the crude product. Recrystallization from benzene yields the desired product.

Workup

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

Sources & evidence

ORD record
ord-89ae654c5085491c809e171d6bf3b7ce
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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