Cyclohexane, (bromomethyl)- → 5-Cyclohexylmethoxy-2-fluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate

HRID 1794116Notes

Reaction equation

HRID 1794116 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][OH:5].[CH:11]1([CH2:17]Br)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Cl[C:20]([N:22]1[C@H:27]([CH3:28])[CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][C@@H:23]1[CH3:36])=[O:21]>>[CH3:36][C@H:23]1[CH2:24][NH:25][CH2:26][C@@H:27]([CH3:28])[N:22]1[C:20]([O:5][CH2:4][C:3]1[CH:6]=[C:7]([O:10][CH2:17][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][C:2]=1[F:1])=[O:21]

Participants

4

Reactant 3

HCID 137636Cyclohexane, (bromomethyl)-HCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 691408025-Cyclohexylmethoxy-2-fluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate

Procedure

5-Cyclohexylmethoxy-2-fluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, cyclohexylmethyl 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 (10.8%); HPLC (XTERRA, 50/80, 220 nm) 91.4% (6.77 min); NMR δH (400 MHz, DMSO-d6) 1.016(2H, m), 1.204(8H, m), 1.735(5H, m), 2.681(4H, m), 3.291(2H, s), 3.737(2H, d, J 6.5 Hz), 3.905(2H, m) 5.078(2H, s), 6.931(2H, m) and 7.119(1H, t, J 9.0 Hz).

Sources & evidence

ORD record
ord-ca0b6954f77a477fbd37d8f08845bf74
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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