Hydrochloric Acid → 2-[4-(Methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine dihydrochloride

HRID 423538Notes

Reaction equation

HRID 423538 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N: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].C(OCC)C>O1CCOCC1>[ClH:32].[ClH:32].[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:15][N:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 249943331,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate

Product 1

HCID 666732092-[4-(Methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine dihydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (5.47 g, 12.25 mmol) in 1,4-dioxane (70 mL) was treated with 4.0M HCl in 1,4-dioxane (30 mL, 122 mmol). The reaction mixture was stirred at ambient temperature for 16 h. Diethyl ether was added to the reaction mixture and the resulting solid was collected by filtration. The crude product was then dissolved in methanol and filtered. The filtrate was concentrated to give 4.36 g (85%) of 2-[4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine dihydrochloride as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.62 (d, 1H, J=2.7 Hz), 8.31 (d, 1H, J=2.7 Hz), 8.23-8.12 (m, 5H), 4.22 (d, 2H, J=6.1 Hz), 3.51-3.46 (m, 2H), 3.20 (s, 3H), 3.13-3.05 (m, 2H), 2.34-2.23 (m, 1H), 2.16-2.10 (m, 2H), 1.75-1.64 (m, 2H); LRMS (APCI), m/z 347 (M+H).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. dissolutionThe crude product was then dissolved in methanol
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-56cb03e7bbc44947b2ed5b98ce598490
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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