HCID 69447489, compound → 4-[1-Methyl-3-(phenylmethyl)-1H-pyrazol-5-yl]piperidine

HRID 1593011Notes

Reaction equation

HRID 1593011 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH3:26])[N:16]=[C:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:19]([C:17]1[CH:18]=[C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[N:15]([CH3:26])[N:16]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 69447489HCID 69447489, compound

Product 1

HCID 181876564-[1-Methyl-3-(phenylmethyl)-1H-pyrazol-5-yl]piperidineYield 78.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(5-Benzyl-2-methyl-2H-pyrazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.032 g) was dissolved in a 25% v/v solution of trifluoroacetic acid in DCM (7 mL) and stirred for 30 minutes. The solvents were then evaporated under reduced pressure to give a clear oil which was purified by column chromatography on SCX-2 stationary phase using a gradient of DCM up to 50% 7N NH3 in MeOH in DCM as eluent. Evaporation of solvent under reduced pressure gave the title compound as a clear oil (0.018 g); NMR(CDCl3): 1.50-1.60 (qd, 2H), 1.85 (br d, 2H), 2.64 (tt, 1H), 2.66-2.76 (qd, 2H), 3.17 (br d, 2H), 3.76 (s, 3H), 3.91 (s, 2H), 5.76 (s, 1H), 7.16-7.20 (m, 1H), 7.24-7.30 (m 4H); MS: 256 (MH+).

Workup

  1. customThe solvents were then evaporated under reduced pressure
  2. customto give a clear oil which
  3. customwas purified by column chromatography on SCX-2 stationary phase
  4. customEvaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-7a5d1461504f4fb39c3830ba5578cf65
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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