Triethylamine → HCID 58010777, compound

HRID 2079285Notes

Reaction equation

HRID 2079285 reaction equation
[OH:1][C@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=O.[CH2:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([C:3](=[O:5])[C@H:2]([OH:1])[CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:19][CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 439960(R)-2-hydroxy-4-methylpentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 58010777HCID 58010777, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-α-hydroxyisocaproic acid (52.1 g, 0.394 mol) was added to a solution of 1-benzylpiperazine (69.46 g, 0.394 mol) in CH2Cl2 (500 mL). The mixture was cooled in ice and Et3N (57 mL, 0.5 mol) was added, followed by HOBt (53.25 g, 0.394 mol) and EDCI.HCl (76.0 g, 0.396 mol). The reaction mixture was allowed to warm to room temperature overnight. The organic layer was washed with water (3×200 mL). The combined aqueous layers were back-extracted with CH2Cl2 (3×25 mL). The combined organic layers were washed with water (3×20 mL), dried over Na2SO4 and concentrated to give 1-(4-benzyl-piperazin-1-yl)-2-(R)-hydroxy-4-methyl-pentan-1-one as a brown oil (109 g, 0.375 mol, 95%). 1H NMR (300 MHz, CDCl3): d 7.35-7.24 (m, 5H); 4.35 (dd, J=10 Hz, 2 Hz, 1H); 3.77-3.55 (m, 4H); 3.52 (s, 2H); 3.36 (m, 2H); 4.45 (m, 4H); 1.97 (m, 1H); 1.47-1.38 (m, 1H); 1.29-1.21 (m, 1H); 0.96 (d, J=6 Hz, 3H); 0.94 (d, J=6 Hz, 3H) ppm.

Workup

  1. temperatureThe mixture was cooled in ice
  2. washThe organic layer was washed with water (3×200 mL)
  3. extractionThe combined aqueous layers were back-extracted with CH2Cl2 (3×25 mL)
  4. washThe combined organic layers were washed with water (3×20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a94137e8904c4e2b8afcf8f7cde65317
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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