3-Fluorobenzyl bromide → HCID 69141024, compound

HRID 1794129Notes

Reaction equation

HRID 1794129 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]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br.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][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([F:11])[CH:13]=2)[CH:8]=[CH:9][C:2]=1[F:1])=[O:22]

Participants

4

Reactant 3

HCID 680073-Fluorobenzyl bromideHCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69141024HCID 69141024, compound

Procedure

2-Fluoro-5-(3-fluorobenzyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, 3-fluorobenzyl bromide and 1-chlorocarbonyl-cis-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the procedures described for Examples 121 and 54 to give the product as a yellow oil: δH (400 MHz, DMSO-d6) 1.28 (6H, d, J 6.9 Hz), 2.77–2.90 (4H, m), 4.10 (2H, br), 5.03 (2H, s), 5.17 (2H, s), 6.85 (1H, m), 6.95–7.10 (3H, m), 7.15 (2H, m) and 7.35 (1H, m), NH not observed; HPLC (XTERRA, 50/80%, 220 nm) 85% (4.83 min).

Sources & evidence

ORD record
ord-32ceb663e44440cc99342f079fb711fb
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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