Hydrochloric Acid → HCID 23294474, compound

HRID 1955191Notes

Reaction equation

HRID 1955191 reaction equation
C([O:8][C:9]1[CH:31]=[CH:30][C:12]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.I[Si](C)(C)C.[ClH:37].CCOCC>C(Cl)(Cl)Cl.CO>[ClH:29].[OH:8][C:9]1[CH:31]=[CH:30][C:12]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH:22]([Cl:37])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 85247Trimethylsilyl iodideHCID 23294406HCID 23294406, compound

Product 1

HCID 23294474HCID 23294474, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6212ChloroformSolvent

Procedure

To a solution of 1-[2-(4-benzyloxyphenoxy)ethyl]-4-(4-chlorobenzyl)piperidine (200 mg, 0.46 mmol) in 5 mL of chloroform was added 330 mg (1.65 mmol) of iodotrimethylsilane. The resulting solution was allowed to stir at rt for 30 min. and then methanol (4 mL) was added and was stirred for 20 min. Evaporation of solvent gave a residue, which was purified by flash chromatography (20% methanol in chloroform) to give an oil. This oil was dissolved into 5 mL of methanol and 1 mL of 1 M HCl in methanol was added. The resulting solution was allowed to stir for 10 min. Evaporation of methanol gave a residue, to which was added ether (30 mL). The resulting mixture was allowed to stir at rt overnight. The white solid was collected by filtration and dried in vacuo, giving 91 mg (52%) of the title compound, mp 168-170° C. 1H NMR (CD3OD) 1.536 (m, 2 H), 1.656 (d, J=12.6 Hz, 3 H), 2.615 (d, J=6.9 Hz, 2 H), 3.060 (m, 2 H), 3.499 (m, 2 H), 3.591 (m, 2 H), 4.245 (t, J=4.8 Hz, 2 H), 6.710 (m, 2 H), 6.823 (m, 2 H), 7.177 (d, J=8.4 Hz, 2 H), 7.280 (d, J=8.1 Hz, 2 H).

Workup

  1. stirringwas stirred for 20 min
  2. customEvaporation of solvent
  3. customgave a residue, which
  4. customwas purified by flash chromatography (20% methanol in chloroform)
  5. customto give an oil
  6. additionwas added
  7. stirringto stir for 10 min
  8. customEvaporation of methanol
  9. customgave a residue
  10. stirringto stir at rt overnight
  11. filtrationThe white solid was collected by filtration
  12. customdried in vacuo

Sources & evidence

ORD record
ord-a4cce69523e44db9a738663076321527
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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