2,6-Lutidine → HCID 87107731, compound

HRID 1624875Notes

Reaction equation

HRID 1624875 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].N1C(C)=CC=CC=1C.[N:14]1([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1>C(Cl)Cl>[ClH:3].[N:14]1([CH:19]2[CH2:24][CH2:23][N:22]([P:1]([Cl:5])([Cl:3])=[O:2])[CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 787034-(1-Pyrrolidinyl)piperidine

Product 1

HCID 87107731HCID 87107731, compoundYield 207%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (ice/water bath) solution of phosphorus oxychloride (5.70 mL, 55.6 mmol) in DCM (30 mL) was added 2,6-lutidine (19.4 mL, 167 mmol) and a DCM solution (30 mL) of 4-(1-pyrrolidinyl)-piperidine (8.58 g, 55.6 mmol) and stirred for 1 hour. The suspension was filtered and solid washed with excess diethyl ether to afford the title pyrrolidine (17.7 g, 91% yield) as a white solid. ESI/MS calcd. for 1-(4-nitrophenyl)piperazine derivative C19H30N5O4P 423.2. found m/z=422.2 (M−1).

Workup

  1. filtrationThe suspension was filtered
  2. washsolid washed with excess diethyl ether

Sources & evidence

ORD record
ord-716595cc053c47a29a90eba504f3cc1b
Source dataset
uspto-grants-2014_07
Patent number
US08779128B2

Reaction notes

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