Piperidine → HCID 86618883, compound

HRID 252406Notes

Reaction equation

HRID 252406 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([CH2:16][CH:17]([CH:31]([CH3:33])[CH3:32])[CH2:18][CH:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]1[CH2:22][O:21]1)[CH:12]=[CH:11]2.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C(O)(C)C>[OH:21][CH:20]([CH:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:18][CH:17]([CH2:16][C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=[CH:8][CH:9]=2)[CH:14]=1)[CH:31]([CH3:32])[CH3:33])[CH2:22][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86618884HCID 86618884, compound

Product 1

HCID 86618883HCID 86618883, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 0.23 g of tert-butyl {3-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-4-methyl-1-oxiranylpentyl}carbamate in 4 ml of isopropanol and 0.99 ml of piperidine is stirred at 70° C. On completion of reaction (TLC monitoring), the reaction mixture is concentrated by evaporation, and the residue is admixed with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. customOn completion of reaction (TLC monitoring)
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. extractionextracted with tert-butyl methyl ether (2×)
  4. washThe combined organic phases are washed successively with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-625a534d678542598593c5f87352e329
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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