Hydrochloric Acid → 4-({[4'-(Methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride

HRID 423455Notes

Reaction equation

HRID 423455 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[ClH:32]>O1CCOCC1.CCOCC>[ClH:32].[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 591777911,1-Dimethylethyl 4-({[4'-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate

Product 1

HCID 666725844-({[4'-(Methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-Dimethylethyl 4-({[4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate (Example 1, 87 mg, 0.20 mmol) was dissolved in 1,4-dioxane (4 mL). Ether (3 mL) was added followed by addition of 4M HCl in 1,4-dioxane (3 mL) and 2M HCl in ether (3 mL). The reaction mixture was stirred at ambient temperature overnight. Ether (15 mL) was added, and the white solid was collected via filtration and washed with ether to yield 71 mg (95%) of 4-({[4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.98 (d, 2H, J=8.5 Hz), 7.83 (d, 2H, J=8.3 Hz), 7.66 (d, 2H, J=8.8 Hz), 7.05 (d, 2H, J=8.8 Hz), 3.97 (d, 2H, J=5.8 Hz), 3.50-3.40 (m, 2H), 3.13 (s, 3H), 3.10-3.00 (m, 2H), 2.25-2.05 (m, 3H), 1.70-1.55 (m, 2H); LRMS (ESI), m/z 346 (M+H).

Workup

  1. filtrationthe white solid was collected via filtration
  2. washwashed with ether

Sources & evidence

ORD record
ord-3f0ed7f2ef0b4e489ad1bb8df55e7f8f
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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