Acetaldehyde → HCID 69420096, compound

HRID 456468Notes

Reaction equation

HRID 456468 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]([NH2:24])[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:25](=O)[CH3:26].[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:29].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]([N:24]([CH2:25][CH3:26])[CH2:28][CH3:29])[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69423162HCID 69423162, compound

Product 1

HCID 69420096HCID 69420096, compoundYield 122.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-[2-(2-Amino-propoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (0.35 g, 0.75 mmol) was dissolved in methanol (25 mL), and the reaction was cooled to 0° C. Acetaldehyde (0.363 g, 8.25 mmol) and sodium triacetoxyborohydride (0.795 g, 3.75 mmol) were added. A reflux condenser was fitted and the flask was stirred at r.t. for about 24 hours. The solution was extracted with diethyl ether (3×50 mL) and then concentrated under reduced pressure to afford the final compound (0.360 g, 90%).

Workup

  1. customA reflux condenser was fitted
  2. extractionThe solution was extracted with diethyl ether (3×50 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7256110be83a4036a7bb43ffff8ef5cf
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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