Trifluoroacetic acid → HCID 57640336, compound

HRID 2111926Notes

Reaction equation

HRID 2111926 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:22][C:23]2[S:24][CH:25]=[CH:26][N:27]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:31][CH:30]([CH3:32])[CH2:29][CH2:28][N:21]([CH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)[CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68577174HCID 68577174, compound

Product 1

HCID 57640336HCID 57640336, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.7 ml, 35 mmol) is added to a solution of 4-{(3-methyl-butyl)-[(thiazol-2-yl)-methyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (0.20 g, 0.55 mmol) in dichloromethane (2.7 ml). The reaction is stirred for 1 hour at room temperature. The reaction is concentrated, loaded onto a SCX-2 (5 g) column, and washed with water (50 ml) and methanol (50 ml). The product is then eluted off with 2M ammonia in methanol (100 ml) and concentrated on a rotary evaporator to yield (0.14 g) of N-(3-methylbutyl)-N-[(1,3-thiazol-2-yl)methyl]piperidin-4-amine: mass spectrum (ion spray): m/z=268 (M+1); 1H NMR (CDCl3): δ=7.67 (1H, d), 7.22 (1H, d), 3.95 (2H, s), 3.16-3.09 (2H, m), 2.67-2.49 (5H, m), 1.81 (2H, brd), 1.69-1.57 (2H, m), 1.50-1.32 (4H, m), 0.87 (6H, d).

Workup

  1. concentrationThe reaction is concentrated
  2. washwashed with water (50 ml) and methanol (50 ml)
  3. washThe product is then eluted off with 2M ammonia in methanol (100 ml)
  4. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-d5d28f21260342d3b69496b5b6d64548
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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