Dicyclohexylcarbodiimide → HCID 21533415, compound

HRID 1657661Notes

Reaction equation

HRID 1657661 reaction equation
[OH:1][C:2]1[C:7]2[C:8]3[CH:16]([CH3:17])[CH2:15][S:14][C:9]=3[C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[C:4]([CH:18]([CH:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH3:19])[CH:3]=1.Cl.[N:28]1([CH2:34][CH2:35][CH2:36][C:37](O)=[O:38])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:26][CH:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:18]([C:4]1[CH:3]=[C:2]([O:1][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:7]2[C:8]3[CH:16]([CH3:17])[CH2:15][S:14][C:9]=3[C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=1)[CH3:19]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 30438811,4,4-Trimethyl-7-(3-methyloctan-2-yl)-1,4-dihydro-2H-thieno[2,3-c][1]benzopyran-9-olHCID 131720814-(Piperidin-1-yl)butanoic acid hydrochloride

Product 1

HCID 21533415HCID 21533415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A combination of 2.4 g. (6.4 mmole) of 1,2-dihydro-9-hydroxy-7-(3-methyl-2-octyl)-1,4,4-trimethyl-4H-thieno[2,3-c][1]benzopyran, 1.33 g. (6.4 mmole) of γ-piperidinobutyric acid hydrochloride, 1.40 g. (6.75 mmole) of dicyclohexylcarbodiimide and 125 ml. of methylene chloride was stirred at room temperature for 18 hours. The reaction mixture was cooled and the byproduct of dicyclohexylurea was removed by filtration. The methylene chloride was distilled off on a rotary evaporator to give a colorless, foamy residue, which was purified on 80 g. of magnesium silicate (60- 100 mesh) using a graded methanol/chloroform solvent system. The fractions were monitored by thin layer chromatography, and the appropriate fractions were combined to give 1.23 g. (37%) of the desired material as a golden gum. The infrared and nuclear magnetic resonance spectra were in agreement with the desired product. Anal. Calcd. for C32H49NO3S (MW = 527.7). C, 72.82; H, 9.36; N, 2.65; Found: C, 72.88; H, 9.40; N, 2.58.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe byproduct of dicyclohexylurea was removed by filtration
  3. distillationThe methylene chloride was distilled off on a rotary evaporator
  4. customto give a colorless, foamy residue, which
  5. customwas purified on 80 g
  6. customto give 1.23 g

Sources & evidence

ORD record
ord-eb99b815f8a14c51a53b1cbd93b5a834
Source dataset
uspto-grants-1976_06
Patent number
US03960871

Reaction notes

Loading…