Cesium carbonate → HCID 70168598, compound

HRID 1387256Notes

Reaction equation

HRID 1387256 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][C:15](OC)=[CH:16][CH:17]=3)[CH:12]=CC=2)=[CH:5][CH:4]=1.[C:21](=[O:24])([O-])[O-].[Cs+].[Cs+].Cl.[Cl:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[C:37]([O:40][CH2:41][CH3:42])(=O)[CH3:38].[OH2:43]>CN(C)C=O>[ClH:28].[N:31]1([CH2:30][CH2:29][O:43][C:3]2[CH:4]=[CH:5][C:37]([O:40][C:41]3[C:42]4[C:16](=[CH:15][C:14]([O:24][CH3:21])=[CH:13][CH:12]=4)[CH:17]=[CH:18][C:9]=3[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[CH:38][CH:8]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 22728543Water ethylacetateHCID 86151826HCID 86151826, compound

Product 1

HCID 70168598HCID 70168598, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-hydroxy)phenoxy-2-(4-methoxy-phenyl-6-methoxynaphthalene (865 mg, 2.32 mmol) in 15 mL of anhydrous N,N-dimethylformamide under N2 was added cesium carbonate (3.0 g, 9.2 mmol). After stirring for 15 minutes, 2-chloroethylpiperidine hydrochloride (540 mg, 2.90 mmol) was added. The resulting mixture was stirred vigorously for 24 hours, then distributed between ethyl acetate/water (200 mL ea.). The layers were separated, and the organic layer was washed several times with water. The organic layer was then dried (sodium sulfate) and concentrated in vacuo to a white solid. The crude free base was dissolved in 20 mL of ethyl acetate and treated with ethyl ether.hydrochloric acid. A precipitate formed that was collected by filtration and dried in vacuo to provide 1.06 g (88%) of 1-[4-[2-(1-piperdinyl)ethoxy]-phenoxy]-2-(4-methoxyphenyl)-6-methoxynaphthalene hydrochloride as a white solid. mp 184-188° C. 1H NMR (DMSO-d6) δ9.91 (bs, 1H), 7.84 (d, J=8.5 Hz, 1H), 7.71 (d, J=9.2 Hz, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.54 (d, J=8.8 Hz, 2H), 7.45 (d, J=2.2 Hz, 1H), 7.15 (dd, J=9.2, 2.2 Hz, 1H), 6.93 (d, J=8.8 Hz, 2H), 6.82 (d, J=9.1 Hz, 2H), 6.61 (d, J=9.1 Hz, 2H), 4.21 (m, 2H), 3.89 (s, 3H), 3.75 (s, 3H), 3.45-3.33 (m, 4H), 2.92 (m, 2H), 1.80-1.63 (m, 5H), 1.35 (m, 1H). FD mass spec: 483. Anal. Calcd. for C31H33NO4.1.0 HCl: C, 71.60; H, 6.59; N, 2.69. Found: C, 71.77; H, 6.66; N, 2.79.

Workup

  1. stirringThe resulting mixture was stirred vigorously for 24 hours
  2. customThe layers were separated
  3. washthe organic layer was washed several times with water
  4. dry with materialThe organic layer was then dried (sodium sulfate)
  5. concentrationconcentrated in vacuo to a white solid
  6. dissolutionThe crude free base was dissolved in 20 mL of ethyl acetate
  7. additiontreated with ethyl ether
  8. customA precipitate formed
  9. filtrationthat was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-458d322db3604a0d9e10805206b33207
Source dataset
uspto-grants-2001_07
Patent number
US06268361B1

Reaction notes

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