6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo(c)chromen-1-ol → 1-[4-(Morpholino)butyryloxy]-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8-tetrahydrodibenzo[b,d]pyran hydrobromide

HRID 267340Notes

Reaction equation

HRID 267340 reaction equation
[OH:1][C:2]1[C:11]2[CH:10]3[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:3]=1.[BrH:24].[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])[CH2:27][CH2:26]1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)Cl>CO.C(Cl)(Cl)Cl>[BrH:24].[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C:34]([O:1][C:2]2[C:11]3[CH:10]4[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]4[C:8]([CH3:17])([CH3:18])[O:7][C:6]=3[CH:5]=[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:3]=2)=[O:35])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 29786,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo(c)chromen-1-olHCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 68121683gamma-Morpholinobutyric acid hydrobromide

Product 1

HCID 214339031-[4-(Morpholino)butyryloxy]-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8-tetrahydrodibenzo[b,d]pyran hydrobromide

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

3.54 g. (11.27 mmole) of 1-Hydroxy-3-n-pentyl-6,6,9-trimethyl-10a,6a ,7,8-tetrahydrodibenzo[ b,d] pyran, 2.86 g. (11.27 mmole) of γ-morpholinobutyric acid hydrobromide and 2.50 g. (12.12 mole) of dicyclohexylcarbodiimide were combined in 200 ml. of methylene chloride and stirred at room temperature for 24 hours. The reaction mixture was cooled and the by-product of dicyclohexylurea was removed by filtration. The volume of methylene chloride was reduced and 25 ml. of cyclohexane was added. The mixture was cooled and the small amount of solid which formed was removed by filtration. All solvents were removed on a rotary evaporation and the residue was dried in vacuo. The resulting foamy material was dissolved in a mixture of benzene and ether and placed in cold storage to yield 3.0 g. (50%) of product as colorless crystals, m.p. 103°-105°C. The compound gave a Rf 0.5 in 5% MeOH/CHCl3. The infrared and nuclear magnetic resonance spectra were consistent with the proposed structure.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe by-product of dicyclohexylurea was removed by filtration
  3. additionof cyclohexane was added
  4. temperatureThe mixture was cooled
  5. customthe small amount of solid which formed
  6. customwas removed by filtration
  7. customAll solvents were removed on a rotary evaporation
  8. customthe residue was dried in vacuo
  9. dissolutionThe resulting foamy material was dissolved in a mixture of benzene and ether
  10. customto yield 3.0 g

Sources & evidence

ORD record
ord-3aeec7074d55418ea1983fa2bc591e43
Source dataset
uspto-grants-1976_03
Patent number
US03941782

Reaction notes

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