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

HRID 2398887Notes

Reaction equation

HRID 2398887 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.[BrH:28].[O:29]1[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][C:38](O)=[O:39])[CH2:31][CH2:30]1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)Cl>CCOCC.CO.C(Cl)(Cl)Cl>[BrH:28].[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:32]2[CH2:31][CH2:30][O:29][CH2:34][CH2:33]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 68121683gamma-Morpholinobutyric acid hydrobromide

Product 1

HCID 214339383-(3-Methyl-2-octyl)-1-[4-(morpholino)butyryloxy]-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran hydrobromide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584188Chloroform methanolSolvent

Procedure

4.12 g. (11.15 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 2.84 g. (11.15 mmole) of γ-morpholinobutyric acid hydrobromide and 2.48 g. (12.0 mmole) of dicyclohexylcarbodiimide in 250 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 golden, viscous residue. The material was dissolved in ether and the solid which appeared was removed by filtration. Recrystallization from benzene/ether gave 2.8 g. (41%) of product as colorless crystals, m.p. 120°-122°. The compound showed an Rf 0.7 in 10 % MeOH/CHCl3 ; the infrared and nmr spectra are consistent with the proposed structure.

Workup

  1. customThe by-product of dicyclohexylurea was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give a golden, viscous residue
  4. customthe solid which appeared was removed by filtration
  5. customRecrystallization from benzene/ether
  6. customgave 2.8 g

Sources & evidence

ORD record
ord-51d6f74efdaf49ee914470406b42bde6
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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