Trifluoroacetic acid → HCID 11413885, compound

HRID 1868101Notes

Reaction equation

HRID 1868101 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:31])([F:30])[C:10]1[C:11]([N:16]2[CH2:21][CH2:20][CH:19]([NH:22]C(=O)OC(C)(C)C)[CH2:18][CH2:17]2)=[N:12][CH:13]=[CH:14][CH:15]=1>C(Cl)Cl>[F:30][C:9]([F:8])([F:31])[C:10]1[C:11]([N:16]2[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 591776761,1-Dimethylethyl N-[1-[3-(trifluoromethyl)-2-pyridinyl]-4-piperidinyl]carbamate

Product 1

HCID 11413885HCID 11413885, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of TFA (10 mL) and CH2Cl2 (10 mL) was added to a flask containing the tert-butyl carbamate from Step 17A (1.39 g, 4.0 mmol). After 1 h, the mixture was concentrated, diluted with CH2Cl2 (100 mL), washed with 1N NaOH (100 mL), H2O (100 mL) and brine (100 mL), dried (MgSO4), and concentrated to afford the amine (0.57 g, 57%), a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.38-1.70 (m, 2H), 1.75-2.08 (m, 2H), 2.44 (br s, 2H), 2.71-3.21 (m, 3H), 3.59 (d, J=13.4 Hz, 2H), 6.76-7.13 (m, 1H), 7.85 (dd, J=7.7, 1.9 Hz, 1H), 8.41 (dd, J=4.8, 1.3 Hz, 1H).

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with CH2Cl2 (100 mL)
  3. washwashed with 1N NaOH (100 mL), H2O (100 mL) and brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-01262806726044a196e96d213c228de7
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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