1-Iodopentane → (R)-2-Fluoro-5-pentyloxybenzyl 2-methylpiperazine-1-carboxylate

HRID 1794130Notes

Reaction equation

HRID 1794130 reaction equation
F[C:2]1C=CC(O)=C[C:3]=1CO.ICCCCC.[CH3:17][C@@H:18]1[CH2:23][NH:22][CH2:21][CH2:20][N:19]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[C:32]([O:34][CH2:35][CH:36]=[CH2:37])[CH:31]=[CH:30][C:29]=1[F:38])=[O:25]>>[CH3:17][C@@H:18]1[CH2:23][NH:22][CH2:21][CH2:20][N:19]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:2][CH3:3])[CH:31]=[CH:30][C:29]=1[F:38])=[O:25]

Participants

4

Reactant 3

HCID 123351-IodopentaneHCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 69142358(R)-2-Fluoro-5-(2-propenyl)oxybenzyl 2-methylpiperazine-1-carboxylate

Product 1

HCID 66838273(R)-2-Fluoro-5-pentyloxybenzyl 2-methylpiperazine-1-carboxylate

Procedure

(R)-2-Fluoro-5-pentyloxybenzyl 2-methylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, 1-iodopentane and (R) 2-methylpiperazine resin according to the procedures described for Example 126 to give the product as a yellow oil: δH (400 MHz, DMSO-d6) 0.89 (3H, t, J 7.0 Hz), 1.24 (3H, d, J 7.1 Hz), 1.30–1.45 (4H, m), 1.70 (2H, pent, J 6.7 Hz), 2.90 (1H, m), 3.0–3.20 (4H, m), 3.92 (3H, m), 4.38 (1H, m), 5.07 (1H, d, J 12.5 Hz), 5.12 (1H, d, J 12.5 Hz), 6.93 (1H, m), 6.98 (1H, m), 7.14 (1H, m), 8.90 (1H, br) and 9.40 (1H, br); HPLC (XTERRA, 50/80%, 220 nm) 84.6% (4.85 min).

Sources & evidence

ORD record
ord-8e7a5422ee8b4b1e938e02a2734915f9
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…