Trifluoroacetic acid → N-Methyl-N-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

HRID 1922656Notes

Reaction equation

HRID 1922656 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:21])[CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:21][N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605945HCID 59605945, compound

Product 1

HCID 43611272N-Methyl-N-(tetrahydro-2H-pyran-4-yl)-4-piperidinamineYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[methyl(tetrahydropyran-4-yl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (101 mg, 0.34 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 Methylpiperidin-4-yl(tetrahydropyran-4-yl)amine as a white solid (66 mg, 97%). 1H NMR (CDCl3, 300 MHz): δ 4.05-3.97 (m, 2H); 3.38 (td, J=10.9, 3.8 Hz, 2H); 3.19 (d, J=12.1 Hz, 2H); 2.84-2.57 (m, 5H); 2.27 (s, 3H); 1.80-1.49 (m, 8H).

Workup

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

Sources & evidence

ORD record
ord-f85606c5f79e44d4879e48104cf5452f
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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