Dicyclohexylcarbodiimide → Nabitan Hydrochloride

HRID 441878Notes

Reaction equation

HRID 441878 reaction equation
[CH3:1][C:2]1([CH3:29])[C:21]2[CH2:22][CH2:23][N:24]([CH2:26][C:27]#[CH:28])[CH2:25][C:20]=2[C:5]2[C:6]([OH:19])=[CH:7][C:8]([CH:10]([CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])=[CH:9][C:4]=2[O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[N:46]1([CH2:52][CH2:53][CH2:54][C:55](O)=[O:56])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1.CO.C(Cl)(Cl)[Cl:61]>C(Cl)Cl.C(Cl)Cl.C1CCCCC1>[ClH:61].[CH3:29][C:2]1([CH3:1])[C:21]2[CH2:22][CH2:23][N:24]([CH2:26][C:27]#[CH:28])[CH2:25][C:20]=2[C:5]2[C:6]([O:19][C:55](=[O:56])[CH2:54][CH2:53][CH2:52][N:46]3[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]3)=[CH:7][C:8]([CH:10]([CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])=[CH:9][C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 990408-(1,2-Dimethylheptyl)-1,3,4,5-tetrahydro-5,5-dimethyl-2-(2-propyn-1-yl)-2H-(1)benzopyrano(4,3-c)pyridin-10-olHCID 131720814-(Piperidin-1-yl)butanoic acid hydrochlorideHCID 21584188Chloroform methanol

Product 1

HCID 39502Nabitan Hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21916607Dichloromethane cyclohexaneSolvent

Procedure

The preparation of this compound was repeated by combining equimolar quantities of 5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine, dicyclohexylcarbodiimide and γ-piperidinobutyric acid hydrochloride in methylene chloride. After stirring for about 16 hours at room temperature, the reaction mixture was cooled, and the by-product of dicyclohexylurea was removed by suction filtration. The mother liquor was evaporated to give a light yellow residue which was dissolved in a methylene chloride/cyclohexane mixture and stored in the cold for 16 hours. A small quantity of additional dicyclohexylurea was removed by filtration, and the solvents were distilled off using a rotary evaporator. The residue which remained was dried in vacuo and crystallized from a mixture of methylene chloride and diethyl ether to give a colorless solid, m.p. 108°-111° C. Thin layer chromatography (10% MeOH/CHCl3) indicated the compound to be pure; the nuclear magnetic resonance and infrared spectra of the material were consistent with the desired product.

Workup

  1. customThe preparation of this compound
  2. temperaturethe reaction mixture was cooled
  3. customthe by-product of dicyclohexylurea was removed by suction filtration
  4. customThe mother liquor was evaporated
  5. customto give a light yellow residue which
  6. customcold for 16 hours
  7. customA small quantity of additional dicyclohexylurea was removed by filtration
  8. distillationthe solvents were distilled off
  9. customa rotary evaporator
  10. customThe residue which remained was dried in vacuo
  11. customcrystallized from a mixture of methylene chloride and diethyl ether
  12. customto give a colorless solid, m.p. 108°-111° C

Sources & evidence

ORD record
ord-b44125b1824c4d3d8089ad2b13e3a1f5
Source dataset
uspto-grants-1977_08
Patent number
US04042694

Reaction notes

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