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 267335Notes

Reaction equation

HRID 267335 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-6a,7,8,10 a-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°C.) and 0.48 g. (2.35 mmoles) of dicyclohexylcarbodiimide 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/petroleum ether gave 0.4 g. of product as colorless crystals, m.p. 99°-101°C. The material was pure by thin layer chromatography (10% MeOH/CHCl3); the infrared and nuclear magnetic resonance spectra were 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/petroleum ether
  10. customgave 0.4 g

Sources & evidence

ORD record
ord-923e5d1ca7174e81b8c0fae6b2bce00d
Source dataset
uspto-grants-1976_03
Patent number
US03941782

Reaction notes

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