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

HRID 2398882Notes

Reaction equation

HRID 2398882 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.[N:25]1([CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)[Cl:53]>CO.C(Cl)(Cl)Cl>[ClH:53].[CH2:19]([C:4]1[CH:3]=[C:2]([O:1][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:11]2[CH:10]3[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]3[C:8]([CH3:17])([CH3:18])[O:7][C:6]=2[CH:5]=1)[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 29786,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo(c)chromen-1-olHCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 131720814-(Piperidin-1-yl)butanoic acid hydrochloride

Product 1

HCID 214339173-n-Pentyl-1-[4-(piperidino)butyryloxy]-6,6,9-trimethyl-10a,6a,7,8-tetrahydrodibenzo[b,d]pyran hydrochloride

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

0.46 g. (1.47 mmoles) of 1-Hydroxy-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8 -tetrahydrodibenzo[b,d]pyran, 0.31 g. (1.47 mmoles) of γ-piperidinobutyric acid hydrochloride and 0.32 g. (1.55 mmoles) of dicyclohexylcarbodiimide were combined in 25 ml. of methylene chloride and stirred at room temperature for 4 hours. The insoluble by-product of dicyclohexylurea was removed by filtration and the methylene chloride was evaporated to give a gummy yellowish residue. The gummy material was triturated several times with petroleum ether and dried in vacuo to give 350 mg. of product as a colorless foam-like solid. The sample was pure by thin-layer chromatography (10% MeOH/CHCl3) and the infrared spectrum was consistent with the proposed structure.

Workup

  1. customThe insoluble by-product of dicyclohexylurea was removed by filtration
  2. customthe methylene chloride was evaporated
  3. customto give a gummy yellowish residue
  4. customThe gummy material was triturated several times with petroleum ether
  5. customdried in vacuo
  6. customto give 350 mg

Sources & evidence

ORD record
ord-3452763f828c4c0cbd48a1a26fc918c0
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

Loading…