Piperidine, 1-(2-chloroethyl)-, hydrochloride → HCID 11235858, compound

HRID 1434431Notes

Reaction equation

HRID 1434431 reaction equation
COC1C=CC(CCC2C=CC(OC)=CC=2)=C(C=1)OC1C=CC(O)=CC=1.Cl.ClCCN1CCCCC1.C[O:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:61][CH2:62][C:63]2[CH:68]=[CH:67][C:66]([O:69]C)=[CH:65][CH:64]=2)=[C:43]([CH:60]=1)[O:44][C:45]1[CH:59]=[CH:58][C:48]([O:49][CH2:50][CH2:51][N:52]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]2)=[CH:47][CH:46]=1.Cl.N1C=CC=CC=1>O1CCCC1>[OH:69][C:66]1[CH:67]=[CH:68][C:63]([CH2:62][CH2:61][C:42]2[CH:41]=[CH:40][C:39]([OH:38])=[CH:60][C:43]=2[O:44][C:45]2[CH:59]=[CH:58][C:48]([O:49][CH2:50][CH2:51][N:52]3[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]3)=[CH:47][CH:46]=2)=[CH:64][CH:65]=1

Participants

6

Reactant 4

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 10176127Pyridinium chlorideHCID 11360078HCID 11360078, compoundHCID 66628061HCID 66628061, compound

Product 1

HCID 11235858HCID 11235858, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
170 °C

Procedure

Synthesized from 4-{5-methoxy-2-[2-(4-methoxyphenyl)ethyl]phenoxy}phenol and 1-(2-chloroethyl)piperidine hydrochloride according to an analogous synthetic method to Preparation Example 40,to 1-{2-{4-{5-methoxy-2-[2-(4-methoxyphenyl)ethyl]phenoxy}phenoxy}ethyl}piperidine (344 mg) was added pyridine hydrochloride (1.2 g), and the solution was stirred for 3 hours and 10 minutes at 170° C. To the reaction solution were added tetrahydrofuran and an aqueous solution of 1N sodium hydroxide, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system) to provide the title compound (111 mg).

Workup

  1. extractionan aqueous solution of 1N sodium hydroxide, the solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-10bc3af8c08a40548d3bf524821caf39
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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