Trifluoroacetic acid → HCID 59605994, compound

HRID 1945504Notes

Reaction equation

HRID 1945504 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:20])[CH:15]2[CH2:19][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>[CH3:20][N:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH:15]1[CH2:19][CH2:18][O:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596055664-[Methyl(tetrahydrofuran-3-yl)amino]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59605994HCID 59605994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[methyl(tetrahydrofuran-3-yl)amino]piperidine-1-carboxylic acid tert-butyl ester (132 mg, 0.46 mmol) and TFA (2 mL) in DCM (5 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(piperidin-4-yl)(tetrahydro-furan-3-yl)amine as a white solid (84 mg, quant.). 1H NMR (CDCl3, 300 MHz): δ 3.98-3.91 (m, 1 H); 3.88-3.83 (m, 1 H); 3.80-3.73 (m, 1 H); 3.61-3.53 (m, 1 H); 3.42-3.35 (m, 1 H); 3.26-3.14 (m, 2 H); 2.71-2.53 (m, 2 H); 2.57-2.46 (m, 1 H); 2.23 (s, 3 H); 2.05-1.97 (m, 1 H); 1.93-1.77 (m, 1 H); 1.78-1.72 (m, 2 H); 1.64-1.49 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-9f01f34fa82c4cc997b68c360a5166e3
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

Loading…