1-(Bromomethyl)-3-(trifluoromethyl)benzene → HCID 69140723, compound

HRID 1794119Notes

Reaction equation

HRID 1794119 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][OH:5].[F:11][C:12]([F:22])([F:21])[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br.Cl[C:24]([N:26]1[C@H:31]([CH3:32])[CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][C@@H:27]1[CH3:40])=[O:25]>>[CH3:40][C@H:27]1[CH2:28][NH:29][CH2:30][C@@H:31]([CH3:32])[N:26]1[C:24]([O:5][CH2:4][C:3]1[CH:6]=[C:7]([O:10][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([C:12]([F:22])([F:21])[F:11])[CH:14]=2)[CH:8]=[CH:9][C:2]=1[F:1])=[O:25]

Participants

4

Reactant 3

HCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69140723HCID 69140723, compound

Procedure

2-Fluoro-5-(3-trifluoromethylbenzyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, 3-trifluoromethylbenzyl bromide and 1-chlorocarbonyl-cis-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the methods described for Examples 54 and 121 to give the product as a yellow oil (10.5%); HPLC (XTERRA, 50/80, 220 nm) 96.9% (6.20 min); NMR δH (400 MHz, DMSO-d6) 1.164(6H, d, J 6.5 Hz), 2.668(4H, m), 3.889(2H, m), 5.082(2H, s), 5.199(2H, s), 7.057(2H, m), 7.175(1H, t, J 6.5 Hz) and 7.688(4H, m).

Sources & evidence

ORD record
ord-b4f7da21eba145a69d58a010c99a3243
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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