3-Fluorobenzyl chloride → 2,6-Difluoro-4-(3-fluorobenzyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate

HRID 1794125Notes

Reaction equation

HRID 1794125 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][OH:5].[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Cl.Cl[C:22]([N:24]1[CH:29]([CH3:30])[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH: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[C:2]([F:1])=[CH:9][C:8]([O:10][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=2)=[CH:7][C:6]=1[F:11])=[O:23]

Participants

4

Reactant 3

HCID 99743-Fluorobenzyl chlorideHCID 22219933rac-tert-butyl (3R,5S)-4-(carboxy)-3,5-dimethylpiperazine-1-carboxylateHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenol

Product 1

HCID 691426792,6-Difluoro-4-(3-fluorobenzyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate

Procedure

2,6-Difluoro-4-(3-fluorobenzyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2,6-difluoro-4-hydroxybenzyl alcohol, 3-fluorobenzyl chloride and 1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the methods described for Example 54 and 121 to give the product as a yellow oil: δH (400 MHz; d6-DMSO) 1.13 (6H, d, J 7.0 Hz), 2.60 (2H, dd, J 12, 4.5 Hz), 2.66 (2H, d, J 12 Hz), 3.77–3.86 (2H, m), 5.03 (2H, s), 5.18 (2H, s), 6.84–6.93 (2H, m), 7.16–7.22 (1H, m), 7.27–7.32 (2H, m) and 7.42–7.49 (1H, m); HPLC (XTERRA, 50–80%, 220 nm) 99.8% (5.96 min).

Sources & evidence

ORD record
ord-f3996aff3ee74aba9b543069427796ae
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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