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

HRID 1657658Notes

Reaction equation

HRID 1657658 reaction equation
[CH3:1][CH:2]1[S:26][C:5]2[C:6]([CH3:25])([CH3:24])[O:7][C:8]3[CH:13]=[C:12]([CH:14]([CH:16]([CH3:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH3:15])[CH:11]=[C:10]([OH:23])[C:9]=3[C:4]=2[CH2:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[ClH:42].[O:43]1[CH2:48][CH2:47][N:46]([CH2:49][CH2:50][CH2:51][C:52](O)=[O:53])[CH2:45][CH2:44]1>C(Cl)Cl>[ClH:42].[CH3:1][CH:2]1[S:26][C:5]2[C:6]([CH3:25])([CH3:24])[O:7][C:8]3[CH:13]=[C:12]([CH:14]([CH:16]([CH3:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH3:15])[CH:11]=[C:10]([O:23][C:52](=[O:53])[CH2:51][CH2:50][CH2:49][N:46]4[CH2:45][CH2:44][O:43][CH2:48][CH2:47]4)[C:9]=3[C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 30438832H-Thieno(2,3-c)(1)benzopyran-9-ol, 1,4-dihydro-7-(1,2-dimethylheptyl)-2,4,4-trimethyl-HCID 127337464-Morpholin-4-Yl-Butyric Acid Hydrochloride

Product 1

HCID 215200001,2-dihydro-2,4,4-trimethyl-9-[4-(morpholino)butyryloxy]-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2-Dihydro-2,4,4-trimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4H-thieno-[2,3-c][1]benzopyran, dicyclohexylcarbodiimide and γ-morpholinobutyric acid hydrochloride are combined in methylene chloride and stirred at room temperature. The insoluble dicyclohexylurea is removed by filtration and the methylene chloride is removed on a rotary evaporator. The residue is crystallized from ether to give 1,2-dihydro-2,4,4-trimethyl-9-[4-(morpholino)butyryloxy]-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran hydrochloride.

Workup

  1. customThe insoluble dicyclohexylurea is removed by filtration
  2. customthe methylene chloride is removed on a rotary evaporator
  3. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-61924c817d034193a99c62dbb202e525
Source dataset
uspto-grants-1976_06
Patent number
US03960871

Reaction notes

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