Dicyclohexylcarbodiimide → 9-[4-(Diethylamino)butyryloxy]-1,2-dihydro-4,4-dimethyl-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran hydrochloride

HRID 1579099Notes

Reaction equation

HRID 1579099 reaction equation
[CH3:1][C:2]1([CH3:25])[C:7]2[S:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:24])=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[ClH:41].[CH2:42]([N:44]([CH2:51][CH3:52])[CH2:45][CH2:46][CH2:47][C:48](O)=[O:49])[CH3:43]>C(Cl)Cl>[ClH:41].[CH2:42]([N:44]([CH2:51][CH3:52])[CH2:45][CH2:46][CH2:47][C:48]([O:24][C:11]1[C:5]2[C:6]3[CH2:10][CH2:9][S:8][C:7]=3[C:2]([CH3:1])([CH3:25])[O:3][C:4]=2[CH:14]=[C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])[CH:12]=1)=[O:49])[CH3:43]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2135232H-Thieno(2,3-c)(1)benzopyran-9-ol, 1,4-dihydro-7-(1,2-dimethylheptyl)-4,4-dimethyl-HCID 137955394-(Diethylamino)butanoic acid hydrochloride

Product 1

HCID 215579049-[4-(Diethylamino)butyryloxy]-1,2-dihydro-4,4-dimethyl-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran hydrochlorideYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 g. (1.39 mmole) of 1,2-dihydro-4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran, 0.31 g. (1.50 mmole; Aldrich Chemical Co.) of dicyclohexylcarbodiimide and 0.272 g. (1.39 mmole) of 4-diethylaminobutyric acid hydrochloride (F. F. Blicke, W. B. Wright, Jr., and M. R. Zienty, J. Amer. Chem. Soc., 63 2488 (1941)) were combined in 30 ml. of methylene chloride and stirred at room temperature for 4 hours. The insoluble by-product of dicyclohexylurea was separated by filtration and the methylene chloride was removed on a rotary evaporator. Attempts to crystallize the material were unsuccessful and 400 mg. (53%) of dark brown residue was obtained. The structure was confirmed by the IR and NMR spectra; and TLC gave Rf 0.5 in 5% MeOH/CHCl3. The acid addition salt may be converted to the free base form by methods well known in the art, and the resulting free base form may then be reacted with another suitable acid to form a different acid addition salt.

Workup

  1. customThe insoluble by-product of dicyclohexylurea was separated by filtration
  2. customthe methylene chloride was removed on a rotary evaporator
  3. customto crystallize the material

Sources & evidence

ORD record
ord-74df4688fe6b477e9a2eacdf1ef14681
Source dataset
uspto-grants-1976_02
Patent number
US03940421

Reaction notes

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