(2-Methoxyethyl)(methyl)amine → tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-{3-[(2-methoxyethyl)methylcarbamoyl]-4-methylbenzyloxy}piperidine-1-carboxylate

HRID 1712428Notes

Reaction equation

Cl[C:2]([C:4]1[CH:5]=[C:6]([CH:42]=[CH:43][C:44]=1[CH3:45])[CH2:7][O:8][CH:9]1[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[CH:17][CH:16]=2)[CH2:13][CH2:12][N:11]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:10]1)=[O:3].[CH3:46][O:47][CH2:48][CH2:49][NH:50][CH3:51]>C1(C)C=CC=CC=1>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][O:25][CH2:24][CH2:23][CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH:14]2[CH2:13][CH2:12][N:11]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:10][CH:9]2[O:8][CH2:7][C:6]2[CH:42]=[CH:43][C:44]([CH3:45])=[C:4]([C:2](=[O:3])[N:50]([CH2:49][CH2:48][O:47][CH3:46])[CH3:51])[CH:5]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The solution of 0.222 g of tert-butyl 3-(3-chlorocarbonyl-4-methylbenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 6 ml of toluene is admixed at 0° C. with the solution of 0.129 g of 2-methoxy-N-methylethylamine in 6 ml of toluene. The reaction mixture is stirred at 0° C. over a further 1 hour and then concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.12 (1:2 EtOAc-heptane); Rt=5.72.

Workup

concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-f41f9a129e954003a1d5770efd65bc32
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790715B2

Reaction notes

Loading…