4-[2-(3,4-Dichlorophenyl)-[1,3]dioxolan-2-yl]piperidine → N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide

HRID 369930Notes

Reaction equation

HRID 369930 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[O:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:20]1([CH3:35])[CH:25]=[CH:24][C:23]([C:26]([NH:28][C@H:29]([CH:33]=O)[CH:30]([CH3:32])[CH3:31])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:14]3[CH2:19][CH2:18][N:17]([CH2:33][CH:29]([NH:28][C:26](=[O:27])[C:23]4[CH:22]=[CH:21][C:20]([CH3:35])=[CH:25][CH:24]=4)[CH:30]([CH3:31])[CH3:32])[CH2:16][CH2:15]3)[O:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 232831594-[2-(3,4-Dichlorophenyl)-[1,3]dioxolan-2-yl]piperidineHCID 53763109N-p-toluoyl valinaldehyde

Product 1

HCID 23283153N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamideYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidine (0.21 g, 0.7 mmol), N-p-toluoyl valinaldehyde (0. 17g, 0.764 mmol), sodium triactetoxy-borohydride (0.22 g, 1.04 mmol) in methylene chloride (20 mL) was stirred overnight under argon. After concentrating the reaction mixture, the residue was stirred with ethyl acetate and dilute aqueous potassium carbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crude was flash chromatographed on flash silica gel with 1% methanol/methylene chloride (containing 1% ammonia) to give N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3 ]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide (0.187g, 0.366 mmoles).

Workup

  1. concentrationAfter concentrating the reaction mixture
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on flash silica gel with 1% methanol/methylene chloride (containing 1% ammonia)

Sources & evidence

ORD record
ord-d2c08ea8c2c440ecb770271c253a9353
Source dataset
uspto-grants-2000_10
Patent number
US06140344

Reaction notes

Loading…