Hydrochloric Acid → HCID 66673101, compound

HRID 423508Notes

Reaction equation

HRID 423508 reaction equation
[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][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[ClH:32]>O1CCOCC1.CCOCC>[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)=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 24994033HCID 24994033, compound

Product 1

HCID 66673101HCID 66673101, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

5-[4-(Methylsulfonyl)phenyl]-2-[(4-piperidinylmethyl)oxy]pyridine dihydrochloride (0.32 g, 94%) was prepared as a light yellow solid from 1,1-dimethylethyl 4-[({5-[4-(methylsulfonyl)phenyl]-2-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (Example 70, 0.36 g, 0.81 mmol), 1,4-dioxane (16 mL), ether (12 mL), 4.0M HCl in 1,4-dioxane (12 mL) and 2M HCl in ether (12 mL) in a manner similar to Example 66, Step 1. 1H NMR (400 MHz, CD3OD): δ 8.48 (d, 1H, J=2.5 Hz), 8.06 (dd, 1H, Ja=8.6 Hz, Jb=2.5 Hz), 8.03 (d, 2H, J=8.5 Hz), 7.86 (d, 2H, J=8.4 Hz), 6.94 (d, 1H, J=8.6 Hz), 4.28 (d, 2H, J=6.1 Hz), 3.50-3.40 (m, 2H), 3.14 (s, 3H), 3.10-3.00 (m, 2H), 2.30-2.15 (m, 1H), 2.15-2.05 (m, 2H), 1.70-1.55 (m, 2H); LRMS (ESI), m/z 347 (M+H).

Sources & evidence

ORD record
ord-0af8055d636c486ea638291c99af177b
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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