2,5-Difluorobenzyl alcohol → 2,5-Difluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride

HRID 1794090Notes

Reaction equation

HRID 1794090 reaction equation
[Cl:1][C:2]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C@@H:5]1[CH3:18])=[O:3].[F:19][C:20]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=1[CH2:22][OH:23]>>[ClH:1].[CH3:18][C@H:5]1[CH2:6][NH:7][CH2:8][C@@H:9]([CH3:10])[N:4]1[C:2]([O:23][CH2:22][C:21]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:20]=1[F:19])=[O:3]

Participants

3

Reactant 2

HCID 5225992,5-Difluorobenzyl alcoholHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 691409372,5-Difluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride

Procedure

2,5-Difluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride was prepared from cis 1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine and 2,5-difluorobenzyl alcohol according to the methods described for Examples 52 and 54 to give the product as a white solid (0.247 g, 77% overall); (Found: C, 52.5; H, 6.1; N, 8.7%. C14H18F2N2O2.HCl requires C, 52.4; H, 6.0; N, 8.7%); δH (400 MHz, DMSO-d6), 9.98 (2H, br),7.29 (3H, m), 5.15 (2H, s), 4.31 (2H, m), 3.15 (2H, d, J 12.8 Hz), 3.06 (2H, dd, J 5 and 13 Hz), and 1.31 (6H, d, J 7.2 Hz).

Sources & evidence

ORD record
ord-e8c4731adf3e4d0a99226eabcdab6471
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…