2-Chlorobenzyl alcohol → 2-Chlorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride

HRID 1794084Notes

Reaction equation

HRID 1794084 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].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[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]=[CH:25][CH:26]=[CH:27][C:20]=1[Cl:19])=[O:3]

Participants

3

Reactant 2

HCID 288102-Chlorobenzyl alcoholHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 691413432-Chlorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride

Procedure

2-Chlorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride was prepared from cis 1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine and 2-chloro-benzyl alcohol according to the methods described for Examples 52 and 54 to give the product as a white solid (0.0901 g, 14% overall); νmax (nujol)/cm−1 3375, 2689, 2577, 1699, 1592, 1380, 1328, and 1300; δH (400 MHz, DMSO-d6) 9.62 (2 H, br), 7.50 (2 H, m), 7.40 (2 H, m), 5.19 (2 H, s), 4.33 (2 H, m), 3.18–3.06 (4 H, m), and 1.31 (6 H, d, J 7.2).

Sources & evidence

ORD record
ord-c211103c826e42b493b5a51a803010d1
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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