1-(3-(Trifluoromethyl)benzyl)piperazine → 1-(2-Oxo-2-{4-[3-(trifluoromethyl)benzyl]piperazin-1-yl}ethyl)-3,3-diphenylpiperidin-2-one

HRID 1667157Notes

Reaction equation

HRID 1667157 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[O:18]=[C:19]1[C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][CH2:22][CH2:21][N:20]1[CH2:37][C:38](O)=[O:39].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[O:39]=[C:38]([N:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:13]=[CH:14][CH:15]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=2)[CH2:8][CH2:9]1)[CH2:37][N:20]1[CH2:21][CH2:22][CH2:23][C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]1=[O:18]

Participants

5

Reactant 3

HCID 20608551-(3-(Trifluoromethyl)benzyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Product 1

HCID 574002361-(2-Oxo-2-{4-[3-(trifluoromethyl)benzyl]piperazin-1-yl}ethyl)-3,3-diphenylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-(trifluoromethyl)benzyl)piperazine (0.395 g, 1.616 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.500 g, 1.616 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.403 g, 2.101 mmol) in dichloromethane (2 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF25-40 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 35 minutes (flow=35 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.40-7.61 (m, 4H), 7.27-7.34 (m, 8H), 7.18-7.25 (m, 2H), 4.23 (s, 2H), 3.64-3.69 (m, 2H), 3.55 (s, 2H), 3.50 (t, J=6.5 Hz, 2H), 3.43-3.49 (m, 2H), 2.60-2.67 (m, 2H), 2.38-2.49 (m, 4H), 1.79-1.89 (m, 2H); MS (ESI+) m/z 536 (M+H)+.

Workup

  1. washthe title compound was eluted
  2. customover 35 minutes

Sources & evidence

ORD record
ord-aaa6eeeac7cc42aa85e082ae09dc980c
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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