Pyridine → HCID 20037297, compound

HRID 1904527Notes

Reaction equation

HRID 1904527 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][OH:20])=[O:12])=[C:4]([F:21])[CH:3]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][O:20][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:12])=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 13883196HCID 13883196, compound

Product 1

HCID 20037297HCID 20037297, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

15.9 g (0.05 mol) of 1-[N-(4-chloro-2-fluoro-5-methoxyphenyl)-carbamoyl]-2-hydroxymethylpiperidine (Example 1) and 4.7 g (0.06 mol) of pyridine are dissolved in 200 ml of toluene, and 6.0 g (0.05mol) of pivaloyl chloride are added dropwise at 20° C. The mixture is stirred for 3 hours at 50° C. and washed with twice 100 ml of water, and the toluene phase is dried over sodium sulfate. After the solvent as been removed, 18.4 g (92% of theory) of 1-[N-(4-chloro-2-fluoro-5-methoxyphenyl)-carbamoyl]-2-pivaloyloxymethylpiperidine are obtained in the form of a colorless viscous oil.

Workup

  1. washwashed with twice 100 ml of water
  2. dry with materialthe toluene phase is dried over sodium sulfate
  3. customAfter the solvent as been removed

Sources & evidence

ORD record
ord-fca1f3c4a6e941afb4df3189020878e2
Source dataset
uspto-grants-1989_06
Patent number
US04838931

Reaction notes

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