Dichloromethane → 3-(3-Methyl-2-octyl)-1-[4-(piperidino)butyryloxy]-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran hydrochloride

HRID 2398888Notes

Reaction equation

HRID 2398888 reaction equation
[OH:1][C:2]1[C:11]2[C:10]3[CH2:12][CH:13]([CH3:16])[CH2:14][CH2:15][C:9]=3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([CH:19]([CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:20])[CH:3]=1.Cl.[N:29]1([CH2:35][CH2:36][CH2:37][C:38](O)=[O:39])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)[Cl:57]>CCOCC.CO.C(Cl)(Cl)Cl>[ClH:57].[CH3:27][CH:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:19]([C:4]1[CH:3]=[C:2]([O:1][C:38](=[O:39])[CH2:37][CH2:36][CH2:35][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:11]2[C:10]3[CH2:12][CH:13]([CH3:16])[CH2:14][CH2:15][C:9]=3[C:8]([CH3:17])([CH3:18])[O:7][C:6]=2[CH:5]=1)[CH3:20]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 362763-(1,2-dimethylheptyl)-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo(b,d)pyran-1-olHCID 131720814-(Piperidin-1-yl)butanoic acid hydrochloride

Product 1

HCID 214338833-(3-Methyl-2-octyl)-1-[4-(piperidino)butyryloxy]-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584188Chloroform methanolSolvent

Procedure

2.5 g. (6.76 mmole) of 1-Hydroxy-3-(3-methyl-2-octyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran was combined with 1.41 g. (6.76 mmole) of γ-piperidinobutyric acid hydrochloride and 1.48 g. (7.16 mmole) of dicyclohexylcarbodiimide in 125 ml. of methylene chloride and stirred at room temperature for 16 hours. The by-product of dicyclohexylurea was removed by filtration and the filtrate was evaporated to give a light brown residue. The residue was dissolved in ether and the small amount of solid which appeared was removed by filtration. The ether was removed on a rotary evaporator and the gummy residue which remained was triturated several times with small quantities of hexane. The material was thoroughly dried to give 2.8 g. (74%) of product as a colorless powder. The material was pure by thin layer chromatography (10% MeOH/CHCl3); the infrared and nmr spectra are consistent with the desired product.

Workup

  1. customThe by-product of dicyclohexylurea was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give a light brown residue
  4. customthe small amount of solid which appeared was removed by filtration
  5. customThe ether was removed on a rotary evaporator
  6. customthe gummy residue which remained was triturated several times with small quantities of hexane
  7. customThe material was thoroughly dried
  8. customto give 2.8 g

Sources & evidence

ORD record
ord-77a2347ba90648f6835c0a53a915a05f
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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