1-Iodopropane → (R)-2,6-Difluoro-4-propoxybenzyl 2-methylpiperazine-1-carboxylate fumarate

HRID 1794103

Reaction equation

HRID 1794103 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH2:9]([C@@H:11]1[CH2:16][NH:15][CH2:14][CH2:13][N:12]1[C:17](OCC1C=CC(OC(F)F)=CC=1)=[O:18])C.I[CH2:32][CH2:33][CH3:34].[F:35][C:36]1[CH:43]=[C:42]([OH:44])[CH:41]=[C:40]([F:45])[C:37]=1[CH2:38][OH:39]>>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH3:9][C@@H:11]1[CH2:16][NH:15][CH2:14][CH2:13][N:12]1[C:17]([O:39][CH2:38][C:37]1[C:36]([F:35])=[CH:43][C:42]([O:44][CH2:32][CH2:33][CH3:34])=[CH:41][C:40]=1[F:45])=[O:18]

Participants

4

Reactant 3

HCID 336431-IodopropaneHCID 21021913(R)-4-Difluoromethoxybenzyl 2-ethylpiperazine-1-carboxylate fumarateHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenol

Product 1

HCID 21021908(R)-2,6-Difluoro-4-propoxybenzyl 2-methylpiperazine-1-carboxylate fumarate

Procedure

(R)-2,6-Difluoro-4-propoxybenzyl 2-methylpiperazine-1-carboxylate fumarate was prepared from (R) 1-chlorocarbonyl-2-methyl-4-tert-butoxycarbonylpiperazine, 1-iodopropane and 2,6-difluoro-4-hydroxybenzyl alcohol according to the methods described for Examples 54 and 96 to give the product as a white solid (19.2%); melting point 193.9–194.0° C.; NMR δH (400 MHz, DMSO-d6) 0.958(3H, t, J 7.5 Hz), 1.140(3H, d, J 7.0 Hz), 1.715(2H, m), 2.817(2H, m), 2.982(2H, m), 3.687(2H, m), 4.097(1H, bs), 5.027(2H, q, J 11.0 Hz), 6.573(2H, s) and 6.773(2H, d, J 10.0 Hz).

Sources & evidence

ORD record
ord-8de8cbb695424bc78d4ab623c845748a
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Linked notes

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