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 hydrochloride

HRID 2398880Notes

Reaction equation

HRID 2398880 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.Cl.[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:53]>CO.C(Cl)(Cl)Cl>[ClH:53].[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 127337464-Morpholin-4-Yl-Butyric Acid Hydrochloride

Product 1

HCID 214338881-[4-(Morpholino)butyryloxy]-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8-tetrahydrodibenzo[b,d]pyran hydrochloride

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

0.7 g. (2.23 mmoles) of 1-Hydroxy-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8 -tetrahydrodibenzo[b,d]pyran, 0.48 g. (2.28 mmoles) of γ-morpholinobutyric acid hydrochloride (Cruickshank and Sheehan, J. Am. Chem. Soc. 83, 2891 (1961), m.p. 180°-182°), and 0.48 g. (2.35 mmoles) of dicyclohexylcarbodiimide (Aldrich) were combined with 35 ml. of methylene chloride and stirred at room temperature for a total of 40 hours. The insoluble by-product of dicyclohexylurea was separated by filtration and the methylene chloride was removed using a rotary evaporator. The resulting residue was dissolved in about 20 ml. of benzene and a small amount of insoluble material was removed by filtration. The benzene was evaporated and the residue dried in vacuo to give 0.7 g. of fluffy, white material. Crystallization from benzene/pet ether gave 0.4 g. of product as colorless crystals, m.p. 99°-101°. The material was pure by thin layer chromatography (10% MeOH/CHCl3); the infrared and nmr spectra are in agreement with the proposed structure.

Workup

  1. customThe insoluble by-product of dicyclohexylurea was separated by filtration
  2. customthe methylene chloride was removed
  3. customa rotary evaporator
  4. dissolutionThe resulting residue was dissolved in about 20 ml
  5. customof benzene and a small amount of insoluble material was removed by filtration
  6. customThe benzene was evaporated
  7. customthe residue dried in vacuo
  8. customto give 0.7 g
  9. customCrystallization from benzene/pet ether
  10. customgave 0.4 g

Sources & evidence

ORD record
ord-4af424c09e3e40fdab3e761bb3bef6a9
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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