Tetrahydrofuran → Ethyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-beta-alaninate

HRID 534870Notes

Reaction equation

HRID 534870 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[N:19]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:20]=[O:21].C(N(CC)CC)C.O1CCCC1>O>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:20]([NH:19][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:21])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733373Ethyl 3-isocyanatopropanoateHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751229Ethyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-beta-alaninateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (400 mg), ethyl 3-isocyanatopropionate (286 mg), triethylamine (0.418 mL), and tetrahydrofuran (20 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (470 mg, 95%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-81fc1d1dc0054f248176030880e2765a
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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