Phenethyl bromide → HCID 21021891, compound

HRID 1794117Notes

Reaction equation

HRID 1794117 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][OH:5].[C:11]1([CH2:17][CH2:18]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl[C:21]([N:23]1[C@H:28]([CH3:29])[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][C@@H:24]1[CH3:37])=[O:22]>>[CH3:37][C@H:24]1[CH2:25][NH:26][CH2:27][C@@H:28]([CH3:29])[N:23]1[C:21]([O:5][CH2:4][C:3]1[CH:6]=[C:7]([O:10][CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][C:2]=1[F:1])=[O:22]

Participants

4

Reactant 3

HCID 7666Phenethyl bromideHCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 21021891HCID 21021891, compound

Procedure

2-Fluoro-5-(2-phenyl)ethoxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, 2-phenylethyl 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 (2.2%); HPLC (XTERRA, 50/80, 220 nm) 87.7% (5.58 min); NMR δH (400 MHz, DMSO-d6) 1.168(6H, d, J 7.0 Hz), 2.685(4H, m), 3.020(2H, t, J 7.0 Hz), 3.915(2H, m), 4.175(2H, t, J 7.0 Hz), 5.079(2H, s), 6.940(2H, m), 7.132(1H, t, J 9.0 Hz), 7.224(1H, m) and 7.308(4H, m).

Sources & evidence

ORD record
ord-d04262eb80f74fffbba5444b29ca68bd
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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