HCID 68504556, compound → Tert-butyl 4-[4-(4-aminobutoxy)phenyl]-3-[1-(3-methoxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethoxy]piperidine-1-carboxylate

HRID 1712425

Reaction equation

HRID 1712425 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]2[O:26][CH2:27][C:28]2[CH:37]=[C:36]3[C:31]([CH2:32][CH2:33][C:34](=[O:43])[N:35]3[CH2:38][CH2:39][CH2:40][O:41][CH3:42])=[CH:30][CH:29]=2)=[CH:9][CH:8]=1)#[N:2]>N.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:15][CH:14]2[O:26][CH2:27][C:28]2[CH:37]=[C:36]3[C:31]([CH2:32][CH2:33][C:34](=[O:43])[N:35]3[CH2:38][CH2:39][CH2:40][O:41][CH3:42])=[CH:30][CH:29]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 68504556HCID 68504556, compound

Product 1

HCID 68501063Tert-butyl 4-[4-(4-aminobutoxy)phenyl]-3-[1-(3-methoxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethoxy]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

The solution of 0.650 g of tert-butyl 4-[4-(3-cyanopropoxy)phenyl]-3-[1-(3-methoxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethoxy]piperidine-1-carboxylate in 10 ml of ammonia (2M in methanol) is hydrogenated in the presence of 0.65 g of Raney nickel at 45° C. over 3 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained as a brown oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.13 (200:20:1 dichloromethane-methanol-conc. ammonia); Rt=4.18.

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-b88c8bcbc21a4c3b92e19aa8715b8a9c
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Linked notes

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