HCID 59713394, compound → HCID 10429879, compound

HRID 2223049Notes

Reaction equation

HRID 2223049 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:26](=[O:35])[C:27]2[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=2)([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=2[CH3:24])[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[CH3:33][C:31]1[CH:32]=[C:27]([CH:28]=[C:29]([CH3:34])[CH:30]=1)[C:26]([C:11]1([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=2[CH3:24])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:35]

Participants

4

Reactant 1

HCID 59713394HCID 59713394, compound

Product 1

HCID 10429879HCID 10429879, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(3,5-dimethyl-benzoyl)-4-(3-methoxy-2-methyl-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester in CH2Cl2 and trifluoroacetic acid (20 mL) was stirred at room temperature for 2 hours. The solvent was removed on a rotary evaporator, and the residue was partitioned between ether (150 mL) and saturated aqueous NaHCO3 (50 mL). Significant amounts of undissolved solid were present. The ether layer was dried over MgSO4 and evaporated to leave N-[4-(3,5-dimethyl-benzoyl)-piperidin-4-yl]-3-methoxy-2-methyl-benzamide (0.50 g) as a solid. Additional product (0.11 g) was obtained by extraction and concentration of the aqueous layer with CH2Cl2 (2×50 mL). 1H NMR (500 MHz, CDCl3) δ(ppm): 7.55 (s, 2H), 7.12 (m, 2H), 6.87 (d, 1H), 6.77 (d, 1H), 6.65 (br, 1H), 3.8 (s, 3H), 3.1 (br, 2H), 2.95 (br, 2H), 2.3 (s, 6H), 2.25 (br s, 4H), 1.94 (s, 3H).

Workup

  1. customThe solvent was removed on a rotary evaporator
  2. customthe residue was partitioned between ether (150 mL) and saturated aqueous NaHCO3 (50 mL)
  3. dry with materialThe ether layer was dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-4c4d2401b3014e6f80c9b5da0c68dd4a
Source dataset
uspto-grants-2008_05
Patent number
US07375093B2

Reaction notes

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