(3-Bromopropyl)benzene → HCID 21021892, compound

HRID 1794118Notes

Reaction equation

HRID 1794118 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][CH2:19]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl[C:22]([N:24]1[C@H:29]([CH3:30])[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][C@@H:25]1[CH3:38])=[O:23]>>[CH3:38][C@H:25]1[CH2:26][NH:27][CH2:28][C@@H:29]([CH3:30])[N:24]1[C:22]([O:5][CH2:4][C:3]1[CH:6]=[C:7]([O:10][CH2:19][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:23]

Participants

4

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 21021892HCID 21021892, compound

Procedure

2-Fluoro-5-(3-phenyl)propoxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, 3-phenylpropyl 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 (2.3%); HPLC (XTERRA, 50/80, 220 nm) 91.1% (6.29 min); NMR δH (400 MHz, DMSO-d6) 7.32–7.10 (6H, m), 6.95 (1H, q, J 3 Hz), 6.91 (1H, dt, J 9, 4 Hz), 5.08 (2H, s), 3.93 (2H, t, J 6.5 Hz), 3.91 (2H,m), 2.73 (2H, t, J 7 Hz), 2.71 (2H, d, J 8.5 Hz), 2.65 (2H, dd, J 12.5, 4.5 Hz), 2.00 (2H, m) and 1.18 (6H, d, J 7 Hz).

Sources & evidence

ORD record
ord-68dcfc5b7d3d418d913b70dc4c8121a3
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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