Trifluoroacetic acid → HCID 59605760, compound

HRID 1922658Notes

Reaction equation

HRID 1922658 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:19])[CH:15]2[CH2:18][O:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][N:14]([CH:15]1[CH2:16][O:17][CH2:18]1)[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59606201HCID 59606201, compound

Product 1

HCID 59605760HCID 59605760, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(methyl(oxetan-3-yl)amino)piperidine-1-carboxylic acid tert-butyl ester (150 mg, 0.55 mmol) and TFA (4 mL) in DCM (10 mL) was stirred at room temperature for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH affording Methyl(oxetan-3-yl)piperidin-4-ylamine as a white solid (94 mg, quant.). 1H NMR (CDCl3, 300 MHz): δ 4.67 (t, J=6.7 Hz, 2H); 4.61 (t, J=6.7 Hz, 2H); 3.97 (p, J=6.7 Hz, 1H); 3.14 (d, J=12.3 Hz, 2H); 2.56 (td, J=12.2, 4.0 Hz, 2H); 2.48-2.26 (m, 2H); 2.22 (s, 3H); 1.63 (d, J=12.3 Hz, 2H); 1.40 (qd, J=12.2, 4.0 Hz, 2H).

Workup

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-c304b05afa49430f810f7122dcba2c7f
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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