Hydrochloric Acid → HCID 70080252, compound

HRID 1955190Notes

Reaction equation

HRID 1955190 reaction equation
[ClH:1].C([O:9][C:10]1[CH:31]=[CH:30][C:13]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:12][CH:11]=1)C1C=CC=CC=1.Cl.[H][H].CCOCC>C(O)C.CO.[Pd]>[ClH:1].[OH:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:21][CH2:22]2)=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 70082160HCID 70082160, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70080252HCID 70080252, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

To a solution of 1-[2-(4-benzyloxyphenoxy)ethyl]-4-benzylpiperidine hydrochloride (401 mg, 1.0 mmol) in 25 mL of ethanol was added 1.0 mL of 1 M HCl in methanol and 100 mg of 10% Pd/C. The resulting mixture was hydrogenated at 30 psi of hydrogen for 2 h. The catalyst was removed through a short column of celite (5 g) and washed with methanol (3×15 mL). The combined flitrate was evaporated in vacuo to give an oil and then ether (30 mL) was added to the residue. The resulting mixture was allowed to stir at rt overnight. The white solid was collected by filtration and dried in vacuo, giving 330 mg (100%) of the title product. mp 212-215° C. 1H NMR (CDCl3 +DMSO-d3) 1.656 (m, 3 H), 1.829 (m, 2 H), 2.425 (s, 2 H), 2.626 (m, 2 H), 3.187 (m, 2 H), 3.4 (brs, 1 H), 4.253 (s, 2 H), 6.549 (m, 4 H), 6.942-7.092 (m, 5 H), 12.0 (brs, 1 H).

Workup

  1. customThe catalyst was removed through a short column of celite (5 g)
  2. washwashed with methanol (3×15 mL)
  3. customThe combined flitrate was evaporated in vacuo
  4. customto give an oil
  5. filtrationThe white solid was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-afbc55a419f04e20bcdc7326ede499b5
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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