Dicyclohexylcarbodiimide → 4,4-Dimethyl-9-[4-(Morpholino)Butyryloxy]-7-(4-Phenyl-1-Methylbutyl)-1,2,3,4-Tetrahydrocyclopenta[c] [1]Benzopyran Hydrochloride

HRID 2071974Notes

Reaction equation

HRID 2071974 reaction equation
[CH3:1][C:2]1([CH3:27])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:26])=[CH:12][C:13]([CH:15]([CH3:25])[CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][C:4]=2[O:3]1.[ClH:28].[O:29]1[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][C:38](O)=[O:39])[CH2:31][CH2:30]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:28].[CH3:27][C:2]1([CH3:1])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:26][C:38](=[O:39])[CH2:37][CH2:36][CH2:35][N:32]3[CH2:31][CH2:30][O:29][CH2:34][CH2:33]3)=[CH:12][C:13]([CH:15]([CH3:25])[CH2:16][CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:14][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 127337464-Morpholin-4-Yl-Butyric Acid HydrochlorideHCID 214097424,4-Dimethyl-9-hydroxy-7-(4-phenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta[c] [1] benzopyran

Product 1

HCID 214097564,4-Dimethyl-9-[4-(Morpholino)Butyryloxy]-7-(4-Phenyl-1-Methylbutyl)-1,2,3,4-Tetrahydrocyclopenta[c] [1]Benzopyran Hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.25 g. (3.5 mmoles) of 4,4-dimethyl-9-hydroxy-7-(4-phenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta[c] [1] benzopyran, 0.76 g. (3.63 mmoles) of γ-morpholinobutyric acid hydrochloride and 0.76 g. (3.70 mmoles) of dicyclohexylcarbodiimide are combined in 75 ml. of methylene chloride and stirred at room temperature for 24 hours. The insoluble by-product of dicyclohexylurea is removed by filtration and the methylene chloride solution is concentrated to 20 ml. Cyclohexane is added until the desired compound is obtained as a colorless solid. Recrystallization from methylene chloride/cyclohexane gives the desired crystalline product.

Workup

  1. customThe insoluble by-product of dicyclohexylurea is removed by filtration
  2. concentrationthe methylene chloride solution is concentrated to 20 ml
  3. additionCyclohexane is added until the desired compound
  4. customis obtained as a colorless solid
  5. customRecrystallization from methylene chloride/cyclohexane
  6. customgives the desired crystalline product

Sources & evidence

ORD record
ord-12bfe367fddd4723994d234042311226
Source dataset
uspto-grants-1977_09
Patent number
US04049653

Reaction notes

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