Potassium Carbonate → Methyl 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

HRID 661236Notes

Reaction equation

HRID 661236 reaction equation
[F:1][C:2]([F:33])([F:32])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][N:14]([C:16](OC3C=CC([N+]([O-])=O)=CC=3)=[O:17])[CH2:13][CH:12]([C:28]([O:30][CH3:31])=[O:29])[CH2:11]2)=[CH:6][CH:5]=1.[OH:34][CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:34][CH:35]1[CH2:40][CH2:39][N:38]([C:16]([N:14]2[CH2:15][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([CH2:3][C:2]([F:32])([F:33])[F:1])=[CH:9][CH:8]=3)[CH2:11][CH:12]([C:28]([O:30][CH3:31])=[O:29])[CH2:13]2)=[O:17])[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 581164903-Methyl 1-(4-nitrophenyl) 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-1,3-dicarboxylate

Product 1

HCID 58116578Methyl 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

1.20 g (2.57 mmol) of the compound from Example 54A, 781 mg (7.72 mmol) of 4-hydroxypiperidine and 533 mg (3.86 mmol) of potassium carbonate were added to 14 ml of DMF and heated in a single-mode microwave (Emrys Optimizer) at 150° C. for 45 min. For workup, the reaction solutions were combined and filtered, and the residue was purified by means of preparative HPLC. Yield: 733 mg (66% of theory)

Workup

  1. filtrationfiltered
  2. customthe residue was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-cae5a252fdfc408eb223babe8622531b
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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