Benzyl Chloride → 5-Benzyloxy-2-fluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride
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](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[F:27][C:28]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][C:29]=1[CH2:30][OH:31]>>[ClH:1].[CH3:10][C@H:9]1[CH2:8][NH:7][CH2:6][C@@H:5]([CH3:18])[N:4]1[C:2]([O:31][CH2:30][C:29]1[CH:32]=[C:33]([O:36][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:34]=[CH:35][C:28]=1[F:27])=[O:3]Participants
4
Procedure
5-Benzyloxy-2-fluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride was prepared from cis 1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine, benzyl chloride and 2-fluoro-5-hydroxybenzyl alcohol according to the methods described for Examples 52, 54 and 96 to give the product as a white solid (0.229 g, 56% overall); (Found; C, 61.5; H, 6.5; N, 6.8%. C21H25FN2O3.HCl requires C, 61.7; H, 6.4; N, 6.85%); δH (400 MHz, DMSO-d6) 9.86 (1H, br), 9.17 (1H, br), 7.45–7.33 (5H, m), 7.17 (1H, t, J 9 Hz), 7.08 (1H, m, J 2.8 Hz), 7.02 (1H, m), 5.12 (2H, s), 5.09 (2H, s), 4.29 (2H, m), 3.15 (2H, d, J 12.8 Hz), 3.06 (2H, dd, J 4.8 and 12.8 Hz), and 1.29 (6H, d, J 7.2 Hz).
Sources & evidence
- ORD record
- ord-4bead062ceea43548a8923c1e2bad040
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022707B2
Reaction notes
Loading…