1-Octanol → HCID 54534880, compound

HRID 1073299Notes

Reaction equation

HRID 1073299 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:35](O)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>C(Cl)Cl.N1(C2C=CN=CC=2)CCCC1>[C:1]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:18])[CH2:13][CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 3

HCID 9571-OctanolHCID 10868DicyclohexylcarbodiimideHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 54534880HCID 54534880, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 755674-PyrrolidinopyridineSolvent

Conditions

Temperature
2.5 °C

Procedure

13.2 parts by weight of 1-carbobenzoxypiperidine-4-carboxylic acid are dissolved in 150 parts by volume of methylene chloride, 8 parts by volume of n-octanol and 0.7 part by weight of 4-pyrrolidinopyridine are added, and the mixture is cooled to 0 to 5° C. 12.0 parts by weight of dicyclohexylcarbodiimide are added, and the mixture is stirred at 5° C. for 2 hours and at room temperature for 4 hours. The mixture is left to stand overnight, the precipitated dicyclohexylurea is filtered off with suction (11.3 parts by weight), the solvent is stripped off in vacuo, the residue is stirred with diisopropyl ether in order to remove residual dicyclohexylurea and filtered, and the solvent is stripped off. 21 parts by weight of an oily residue are obtained. The residue is chromatographed on 1070 parts by weight of silica gel using CH2Cl2 /5% of methanol. 9.8 parts by weight of the compound (A) are obtained as an oil. ##STR42## 4-decyloxyphenoxy(4-benzoyl) chloroformate =(B)

Workup

  1. additionare added
  2. waitThe mixture is left
  3. waitto stand overnight
  4. filtrationthe precipitated dicyclohexylurea is filtered off with suction (11.3 parts by weight)
  5. stirringthe residue is stirred with diisopropyl ether in order
  6. customto remove residual dicyclohexylurea
  7. filtrationfiltered
  8. custom21 parts by weight of an oily residue are obtained
  9. customThe residue is chromatographed on 1070 parts by weight of silica gel

Sources & evidence

ORD record
ord-f791ce0f76aa475ba378c32a0c180bd0
Source dataset
uspto-grants-1990_11
Patent number
US04968798

Reaction notes

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