Trifluoroacetic acid → N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide

HRID 1678407Notes

Reaction equation

HRID 1678407 reaction equation
CC([CH:5]1[CH2:10][CH:9]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[O:12])[CH2:8][CH2:7][N:6]1C([O-])=O)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH2:14][NH:13][C:11]([CH:9]1[CH2:10][CH2:5][NH:6][CH2:7][CH2:8]1)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866443111,1-Dimethylethyl-4-({[(2,4-dichlorophenyl)methyl]amino}carbonyl)-1-piperidinecarboxylate

Product 1

HCID 20298096N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500 mL round bottom flask equipped with a magnetic stir bar was charged with 1,1-di methylethyl-4-({[(2,4-dichlorophenyl)methyl]amino}carbonyl)-1-piperidinecarboxylate (27.6 g, 71.2 mmol) and DCM (117 mL) at room temperature. Trifluoroacetic acid (117 mL) was added slowly, and the reaction was maintained at room temperature for 1 hour after which time LC/MS determined that the reaction was complete (Rt=6.03 min and m/e 287 [M+1]+). The volatiles were removed by rotary evaporation and the crude oil was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution (3×200 mL). The organic phase was dried over Na2SO4, filtered and concentrated to give 13.5 g of the title compound (47 mmol, 66%) as a pale yellow solid. MS (ES) m/e 287 [M+H]+. 1H NMR (400 MHz, DMSO-D6) □ 8.6 (m, 1H), 7.4 (d, 1H), 7.3 (d, 1H), 4.3 (m, 2H), 3.2 (m, 2H), 2.8 (m, 2H), 2.5 (m, 1H shouldering on DMSO peak), 1.8 (m, 2H), 1.7 (m, 2H)

Workup

  1. customA 500 mL round bottom flask equipped with a magnetic stir bar
  2. customThe volatiles were removed by rotary evaporation
  3. dissolutionthe crude oil was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution (3×200 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-da9a655461584602bbfed225c742a62c
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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