Piperidin-3-ylmethanol → HCID 13422591, compound

HRID 1284455Notes

Reaction equation

HRID 1284455 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][O:6][C:5]([C:9]([CH3:19])([CH3:18])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)([CH3:8])[O:4]1.[OH:20][CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]1>C(O)C.[I-].[K+]>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:9]([C:5]2([CH3:8])[O:4][CH:3]([CH2:2][N:24]3[CH2:25][CH2:26][CH2:27][CH:22]([CH2:21][OH:20])[CH2:23]3)[CH2:7][O:6]2)([CH3:19])[CH3:18])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 107308Piperidin-3-ylmethanolHCID 13422590HCID 13422590, compound

Product 1

HCID 13422591HCID 13422591, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 702EthanolSolvent

Procedure

30.3 g (0.1 mol) of 4-chloromethyl-2-[1-(4-chlorophenyl)-2-methyl-prop-2-yl]-2-methyl-1,3-dioxolane, 23 g (0.2 mol) of 3-hydroxymethylpiperidine and 0.1 g of potassium iodide in 100 ml of ethanol are heated at 150° C. under pressure (2 bar) for 15 hours. For working up, the solvent is removed in vacuo, the residue is taken up in 100 ml of methylene chloride, the mixture is washed twice with 100 ml of water each time and dried over sodium sulphate and the solvent is removed again in vacuo. 38 g (100% of theory) of 2-[1-(4-chlorophenyl)-2-methyl-prop-2-yl]-4-[(3-hydroxymethylpiperidin-1-yl)-methyl]-2-methyl-1,3-dioxolane of refractive index n20 1.5226 are obtained.

Workup

  1. customthe solvent is removed in vacuo
  2. washthe mixture is washed twice with 100 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed again in vacuo

Sources & evidence

ORD record
ord-977c5dd771844bb683a23d08b3b3b4d7
Source dataset
uspto-grants-1986_01
Patent number
US04563447

Reaction notes

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