Acetic Acid → HCID 57478572, compound

HRID 2218975Notes

Reaction equation

HRID 2218975 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][CH2:15][C:16](=O)[CH2:17]C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:15]([CH2:16][CH3:17])[CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7288Ethyl ketoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57478572HCID 57478572, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of piperazine-1-carboxylic acid tert-butyl ester (7.00 g), 3-pentanone (3.89 g), glacial acetic acid (2.22 mL) and sodium triacetoxyborohydride (11.95 g) in dichloromethane (DCM, 200 mL) was stirred for 18 h at room temperature. The reaction mixture was quenched with 1 N aqueous NaOH (80 mL) and stirred for 2.5 h at room temperature. Additional water (100 mL) was added, and the resulting mixture was extracted with DCM (3×100 mL). Extracts were combined and washed with water (2×100 mL), dried (Na2SO4), and concentrated under reduced pressure, yielding the title compound (6.28 g).

Workup

  1. customThe reaction mixture was quenched with 1 N aqueous NaOH (80 mL)
  2. stirringstirred for 2.5 h at room temperature
  3. additionAdditional water (100 mL) was added
  4. extractionthe resulting mixture was extracted with DCM (3×100 mL)
  5. washwashed with water (2×100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d354cd536034b1589bd26c0caba6fdf
Source dataset
uspto-grants-2008_08
Patent number
US07414047B2

Reaction notes

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