Trifluoroacetic acid → HCID 59756883, compound

HRID 2196599Notes

Reaction equation

HRID 2196599 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:22]C(=O)OC(C)(C)C)[CH2:18][CH2:17]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([NH2:22])[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59756879HCID 59756879, compound

Product 1

HCID 59756883HCID 59756883, compoundYield 71,887,552%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-ylcarbamate (1 g, 2.49 nmol) was dissolved in DCM (25 mL). While stirring, TFA (1.9 mL, 25 mmol) was added dropwise at rt, and the reaction was allowed to stir for 15 hours. The solvent was removed and the crude compound was taken up in EtOAc (150 mL) and washed with sat. sodium bicarbonate (20 mL). The organics were washed with brine, dried with sodium sulfate, and concentrated. The mixture was columned using 100% DCM to 7% MeOH to give the desired product 1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-amine (0.54 g, 1.79 mmol, 72% yield). MS (ESI pos. ion) m/z: 302.2 (MH+). Calc'd exact mass for C17H23N3O2: 301. 1HNMR (400 MHz, CDCl3): 8.63-8.64 (d, J=4.4 Hz, 1H), 7.63 (s, 1H), 7.41 (s, 1H), 7.22-7.23 (d, J=4.4 Hz, 1H), 4.03 (s, 3H), 4.01 (s, 3H), 3.83 (s, 2H), 2.84-2.87 (bd, J=12.0 Hz, 2H), 2.70-2.73 (m, 1H), 2.11-2.16 (bt, J=11.2 Hz, 2H), 1.78-1.82 (bd, J=12.8 Hz, 2 H), 1.37-1.41 (m, 2H).

Workup

  1. stirringto stir for 15 hours
  2. customThe solvent was removed
  3. washwashed with sat. sodium bicarbonate (20 mL)
  4. washThe organics were washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5b2a5be1829a45ec89c472b81e382045
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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