2-Chloro-6-fluorobenzyl alcohol → HCID 69143880, compound

HRID 1794113Notes

Reaction equation

HRID 1794113 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][OH:5].Cl[C:12]([N:14]1[C@H:19]([CH3:20])[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C@@H:15]1[CH3:28])=[O:13]>>[ClH:1].[CH3:28][C@H:15]1[CH2:16][NH:17][CH2:18][C@@H:19]([CH3:20])[N:14]1[C:12]([O:5][CH2:4][C:3]1[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1])=[O:13]

Participants

3

Reactant 2

HCID 918682-Chloro-6-fluorobenzyl alcoholHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69143880HCID 69143880, compound

Procedure

2-Chloro-6-fluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride was prepared from 2-chloro-6-fluorobenzyl alcohol and 1-chlorocarbonyl-cis-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the methods described for Examples 52 and 54 to give the product as a white solid (0.2713 g, 80% overall); (Found: C, 49.8; H, 5.7; N, 8.0%. C14H18ClN2O2.HCl requires C, 49.9; H, 5.7; N, 8.3%); δH (400 MHz, DMSO-d6) 10.01 (1H, br), 9.27 (1H, br), 7.49 (1H, m, J 8.0 Hz), 7.40 (1H, d, J 8.0 Hz), 7.30 (1H, t, J 9 Hz), 5.22 (2H, d, J 1.6 Hz), 4.24 (2H, m, J 6.5 Hz), 3.17–3.06 (4H, m), and 1.28 (6H, d, J 7.2 Hz).

Sources & evidence

ORD record
ord-538395252dd748f09a981a961a156000
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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