Hydrochloric Acid → HCID 66672772, compound

HRID 423502Notes

Reaction equation

HRID 423502 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]1.[ClH:33]>O1CCOCC1.CCOCC>[ClH:33].[F:1][C:2]1[CH:3]=[C:4]([C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:27][CH:28]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 24993711HCID 24993711, compound

Product 1

HCID 66672772HCID 66672772, compoundYield 88%

Reagents, catalysts & solvents 2

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

Procedure

4-({[3-Fluoro-4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride (0.23 g, 88%) was prepared as a white solid from 1,1-dimethylethyl 4-({[3-fluoro-4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate (Example 64, 0.30 g, 0.65 mmol), 1,4-dioxane (12 mL), ether (9 mL), 4.0M HCl in 1,4-dioxane (9 mL) and 2M HCl in ether (9 mL) in a manner similar to Example 66, Step 1. 1H NMR (400 MHz, CD3OD): δ 7.99 (d, 2H, J=8.5 Hz), 7.84 (d, 2H, J=8.5 Hz), 7.55-7.45 (m, 2H), 7.25-7.20 (m, 1H), 4.04 (d, 2H, J=5.9 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), 1.75-1.60 (m, 2H); LRMS (ESI), m/z 364 (M+H).

Sources & evidence

ORD record
ord-51728be8eb3f4b3cbc2f8615a719b61a
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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