Benzyl Alcohol → Benzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride

HRID 1794083Notes

Reaction equation

HRID 1794083 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].[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[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:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:3]

Participants

3

Reactant 2

HCID 244Benzyl AlcoholHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69142638Benzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride

Procedure

Benzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride was prepared from cis 1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine and benzyl alcohol according to the methods described for Examples 52 and 54 to give the product as a cream solid (0.0833 g, 15% overall); νmax (nujol)/cm−1 2776, 2672, 2568, 2527, 1706, 1581, 1415, and 1329; δH (400 MHz, DMSO-d6) 9.89 (1 H, br), 9.19 (1 H, br), 7.41–7.31 (5H, m), 5.13 (2 H, s), 4.34 (2 H, m), 3.17–3.08 (4 H, m), and 1.31 (6 H, d, J 7.2).

Sources & evidence

ORD record
ord-401117db35a74fc4b616d2c73a785576
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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