Hydrochloric Acid → 4,4-Dimethyl-7-(4-p-Fluorophenyl-1-Methylbutyl)-9-[3-(Piperidino)-Propionyloxy]-1,2,3,4-Tetrahydrocyclopenta[c] [1]Benzopyran Hydrochloride

HRID 2071971Notes

Reaction equation

HRID 2071971 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]([CH:15]([CH3:26])[CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:14][C:4]=2[O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[ClH:44].[N:45]1([CH2:51][CH2:52][C:53](O)=[O:54])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1.Cl>CCOCC.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:53](=[O:54])[CH2:52][CH2:51][N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)=[CH:12][C:13]([CH:15]([CH3:26])[CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:14][C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 131319213-(Piperidin-1-yl)propanoic acid hydrochlorideHCID 214097494,4-Dimethyl-9-hydroxy-7-(4-p-fluorophenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta [c] [1]benzopyran

Product 1

HCID 681220344,4-Dimethyl-7-(4-p-Fluorophenyl-1-Methylbutyl)-9-[3-(Piperidino)-Propionyloxy]-1,2,3,4-Tetrahydrocyclopenta[c] [1]Benzopyran Hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3.12 g. (8.2 mmoles) of 4,4-dimethyl-9-hydroxy-7-(4-p-fluorophenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta [c] [1]benzopyran, prepared according to the method of Example 6, 1.77 g. (8.6 mmoles) of dicyclohexylcarbodiimide and 1.65 g. (8.5 mmoles) of β-piperidinopropionic acid hydrochloride (m.p. 216° - 220°, J. Am. Chem. Soc. 73, 3168 (1951) are combined with 125 ml. of methylene chloride and stirred at room temperature for about 20 hours. The reaction mixture is filtered and the methylene chloride removed using a rotary evaporator. The residue is treated with benzene and filtered to remove a small quantity of insoluble material. The benzene is evaporated and the dark, viscous residue is chromatographed using 100 g. of 60 - 100 mesh Florosil activated magnesium silicate and methanol/chloroform graded solvent mixtures. Chromatography yields an oil which is dissolved in ether and treated with a solution of ethereal HCl. The desired compound appears as crystals which are filtered and washed with additional ether to obtain the desired product.

Workup

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

Sources & evidence

ORD record
ord-0916fbefc212497d9e5e646c287c8907
Source dataset
uspto-grants-1977_09
Patent number
US04049653

Reaction notes

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