3-(Chloromethyl)pyridine hydrochloride → HCID 69141099, compound

HRID 1794121Notes

Reaction equation

HRID 1794121 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]=[C:14]([CH2:18]Cl)[CH:13]=1.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:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:9][C:2]=1[F:1])=[O:22]

Participants

4

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69141099HCID 69141099, compound

Procedure

2-Fluoro-5-(3-pyridylmethyl)oxybenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, 3-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 (5.4%); HPLC (XTERRA, 50/80, 220 nm) 91% (1.64 min); δH (400 MHz, DMSO-d6) 1.172 (6H, d, J 7.0 Hz), 2.673 (4H, m), 3.294 (3H, s), 3.900 (2H, m), 5.075 (2H, s), 5.138 (2H, s), 7.052 (2H, m), 7.172 (1H, t, J 9.0 Hz), 7.424 (1H, m), 7.849 (1H, m), 8.546 (1H, m) and 8.654 (1H, m).

Sources & evidence

ORD record
ord-0132c8ca31fd453fb53a5b5ee0cafce9
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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