Water → 1-Acetyl-N-{3-[4-(4-aminoanilino)-1-piperidinyl]propyl}-N-(3,4-dichlorophenyl)-4-piperidinecarboxamide

HRID 412943

Reaction equation

HRID 412943 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].C(OCC)(=O)C.O>C(OC(C)C)(C)C.CCCCCC.[Ni](Br)Br>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([N:12]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=3)[CH2:20][CH2:21]2)[C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)=[O:11])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 185390691-Acetyl-N-(3,4-dichlorophenyl)-N-{3-[4-(4-nitroanilino)-1-piperidinyl]propyl}-4-piperidinecarboxamide

Product 1

HCID 185388641-Acetyl-N-{3-[4-(4-aminoanilino)-1-piperidinyl]propyl}-N-(3,4-dichlorophenyl)-4-piperidinecarboxamideYield 65.4%

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 21881879Diisopropylether hexaneSolvent

Procedure

To a solution of the compound obtained in Example 219 (162 mg, 0.26 mmol) in methanol/THF (1/1, 10 mL) were added nickel bromide (II)(5.7 mg) and sodium borohydride (40 mg, 1.1 mmol), and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture were added ethyl acetate (20 mL) and water (20 mL), and the insolubles were filtered off with Celite. The organic layer was washed with saturated aqueous solution of sodium chloride (10 ml), dried with anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to flash column chromatography (alumina 2 g, ethyl acetate/methanol=1/0 to 10/1), and the desired fraction was concentrated under reduced pressure to give the titled compound (99 mg, 0.17 mmol, Yield 64%) as pale yellow amorphous substance.

Workup

  1. filtrationthe insolubles were filtered off with Celite
  2. washThe organic layer was washed with saturated aqueous solution of sodium chloride (10 ml)
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0cc3015dd9da46a6bd9631c66d71c1b9
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Linked notes

Loading…