Dichloromethane → 1,2-Dihydro-5,5-dimethyl-8-(3-methyl-2-octyl)-10-[2-methyl-4-(piperidino)butyryloxy]-3H,5H-thiopyrano[2,3-c][1]benzopyran hydrochloride

HRID 1657655Notes

Reaction equation

HRID 1657655 reaction equation
[CH3:1][C:2]1([CH3:26])[C:7]2[S:8][CH2:9][CH2:10][CH2:11][C:6]=2[C:5]2[C:12]([OH:25])=[CH:13][C:14]([CH:16]([CH:18]([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:17])=[CH:15][C:4]=2[O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH3:43][CH:44]([CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1)[C:45](O)=[O:46].C(Cl)[Cl:57]>CO.C(Cl)(Cl)Cl>[ClH:57].[CH3:26][C:2]1([CH3:1])[C:7]2[S:8][CH2:9][CH2:10][CH2:11][C:6]=2[C:5]2[C:12]([O:25][C:45](=[O:46])[CH:44]([CH3:43])[CH2:48][CH2:49][N:50]3[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]3)=[CH:13][C:14]([CH:16]([CH:18]([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:17])=[CH:15][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 654438-(1,2-Dimethylheptyl)-1,2,3,5-tetrahydro-5,5-dimethylthiopyrano(2,3-c)(1)benzopyran-10-olHCID 211526892-Methyl-4-piperidin-1-yl-butyric acid hydrochloride

Product 1

HCID 215199981,2-Dihydro-5,5-dimethyl-8-(3-methyl-2-octyl)-10-[2-methyl-4-(piperidino)butyryloxy]-3H,5H-thiopyrano[2,3-c][1]benzopyran hydrochloride

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A combination of 0.5 g. (1.33 mmole) of 1,2-dihydro-5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-3H,5H-thiopyrano [2,3-c][1]benzopyran, 0.30 g. (1.45 mmole) of dicyclohexylcarbodiimide, 0.29 g. (1.33 mmole) of 2-methyl-4-piperidinobutyric acid hydrochloride and 25 ml. of methylene chloride was stirred at room temperature for 16 hours. The reaction mixture was cooled for several hours and the byproduct of dicyclohexylurea was removed by filtration. After removal of the solvent on a rotary evaporator, the residue was combined with 15 ml. of diethyl ether and an additional amount of the dicyclohexylurea was removed by filtration. The solvent was evaporated and the residue thoroughly dried to give 0.40 g. (50%) of beige solid. The sample was pure by thin layer chromatography (10% MeOH/CHCl3), and the infrared spectrum was consistent with the desired product. Anal. Calcd. for C33H52ClNO3S.H2O (MW=596.28) C, 66.44, H, 9.13; N, 2.35; Found: C, 65.84; H, 9.01; N, 2.70.

Workup

  1. temperatureThe reaction mixture was cooled for several hours
  2. customthe byproduct of dicyclohexylurea was removed by filtration
  3. customAfter removal of the solvent
  4. customon a rotary evaporator
  5. customof diethyl ether and an additional amount of the dicyclohexylurea was removed by filtration
  6. customThe solvent was evaporated
  7. customthe residue thoroughly dried
  8. customto give 0.40 g

Sources & evidence

ORD record
ord-7b0283ce77ee43a5a911ceffbd8a29ca
Source dataset
uspto-grants-1976_06
Patent number
US03960871

Reaction notes

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