Trifluoroacetic acid → 2-[4-(Methylsulfonyl)phenyl]-5-(4-piperidinylmethoxy)pyridine

HRID 423692Notes

Reaction equation

HRID 423692 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10]>C(Cl)Cl>[CH3:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:22][N:23]=2)=[CH:14][CH:13]=1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 249943331,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate

Product 1

HCID 597185862-[4-(Methylsulfonyl)phenyl]-5-(4-piperidinylmethoxy)pyridineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL) was added to a solution of 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (705 mg, 1.58 mmol) in CH2Cl2 (50 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The mixture was concentrated, and the crude product was purified by chromatography on a silica gel column using 0 to 10% MeOH/CH2Cl2 give 460 mg (84%) of 2-[4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (d, 1H, J=2.9 Hz), 8.29 (d, 2H, J=8.6 Hz), 8.08 (d, 1H, J=8.8 Hz), 8.00 (d, 2H, J=8.6 Hz), 7.55 (dd, 1H, Ja=8.8 Hz, Jb=3.0 Hz), 4.04 (d, 2H, J=6.2 Hz), 3.40-3.25 (m, 2H), 3.25 (s, 3H), 3.01-2.83 (m, 2H), 2.22-2.02 (m, 1H), 2.00-1.90 (m, 2H), 1.60-1.37 (m, 2H); LRMS (ESI), m/z 347 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-0d5158fe730644ef896a5917925bedec
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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