Picolyl chloride hydrochloride → HCID 69141161, compound

HRID 1794120Notes

Reaction equation

HRID 1794120 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][OH:5].Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]Cl.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][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)[CH:8]=[CH:9][C:2]=1[F:1])=[O:22]

Participants

4

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69141161HCID 69141161, compound

Procedure

2-Fluoro-5-(2-pyridylmethyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, 2-pyridylmethyl chloride hydrochloride 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 (10.4%); HPLC (XTERRA, 50/80, 220 nm) 91.1% (2.02 min); NMR δH (400 MHz, DMSO-d6) 1.174 (6H, d, J 6.5 Hz), 2.676 (4H, m), 3.902 (2H, m), 5.069 (2H, s), 5.165 (2H, s), 7.018 (2H, m), 7.161 (1H, t, J 9.0 Hz), 7.350 (1H, m), 7.493 (1H, d, J 7.0 Hz), 7.825 (1H, m) and 8.575 (1H, m).

Sources & evidence

ORD record
ord-617e1db834fb40e4885de8ae92003812
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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