Triethylamine → Methyl 2-(1,4-dibenzylpiperazin-2-yl)acetate

HRID 23207

Reaction equation

HRID 23207 reaction equation
N1(CC(O)=O)CCNCC1.[CH2:11]([NH:18][CH2:19][CH2:20][NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC.Br[CH2:37]/[CH:38]=[CH:39]/[C:40]([O:42][CH3:43])=[O:41]>C1(C)C=CC=CC=1>[CH2:11]([N:18]1[CH2:19][CH2:20][N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:37][CH:38]1[CH2:39][C:40]([O:42][CH3:43])=[O:41])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8793BenzathineHCID 650402Piperazin-1-yl-acetic acidHCID 53691752-Butenoic acid, 4-bromo-, methyl ester

Product 1

HCID 22710010Methyl 2-(1,4-dibenzylpiperazin-2-yl)acetateYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The piperazineacetic acid compound of formula (XXIV) employed in the synthesis above and many others in this application was synthesized as follows: Twelve milliliters (50 mmol) of N,N′-dibenzylethylene-diamine, 14 mL (100 mmol) of Et3N and 250 mL toluene were combined at 0° C., and 7 mL (50 mmol) of methyl 4-bromocrotonate (7 mL, 50 mmol) was added. The reaction was slowly warmed to room temperature, stirred for 24 hours, filtered, concentrated in vacuo to a residue and treated with 10% aqueous HCl (300 mL). The mixture was filtered again and the filtrate washed with ethyl acetate (2×100 mL). The filtrate was made basic with K2CO3 and extracted with ethyl acetate (3×150 mL). The combined extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to give 13.7 g of methyl 1,4-dibenzylpiperazine-2-acetate. 1H NMR (CDCl3) δ 2.28-2.50 (m,4), 2.5-2.75 (m,4), 3.1 (bs, 1), 3.42 (d,2), 3.52 (d,1), 3.6 (s,3), 3.75 (d,1), 7.15-7.35 (m,1).

Workup

  1. customwas synthesized
  2. customwere combined at 0° C.
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a residue
  5. additiontreated with 10% aqueous HCl (300 mL)
  6. filtrationThe mixture was filtered again
  7. washthe filtrate washed with ethyl acetate (2×100 mL)
  8. extractionextracted with ethyl acetate (3×150 mL)
  9. washThe combined extracts were washed with brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6500e393bc29458f9d864d8919c2c504
Source dataset
uspto-grants-2005_02
Patent number
US06849739B2

Linked notes

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