Triethylamine → HCID 86600952, compound

HRID 1783381Notes

Reaction equation

HRID 1783381 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)=[C:2]=[O:3].[N:11]1([C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([NH:1][C:2]([N:14]2[CH2:13][CH2:12][N:11]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=3)[CH2:16][CH2:15]2)=[O:3])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 693254-Methylphenyl isocyanateHCID 2761178Ethyl 4-(piperazin-1-yl)benzoate

Product 1

HCID 86600952HCID 86600952, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-isocyanato-4-methyl-benzene (0.051 mol) in DCM p.a. (75 ml) was added dropwise to a solution of 4-(1-piperazinyl)-benzoic acid, ethyl ester (0.043 mol) and triethylamine (0.051 mol) in DCM p.a. (75 ml) while stirring at 0° C. (ice) for 20 minutes. The reaction mixture was stirred at room temperature for 1 hour and was then extracted with water. The organic layer was extracted with a saturated NaCl-solution and again with water, then separated, dried (MgSO4), filtered off and the filtrate was evaporated. The residue was stirred in DIPE and the formed precipitate was filtered off, washed with DIPE and dried. A part (0.5 g) of the residue (14.3 g, 90%) was crystallized from 2-propanol (10 ml) and the formed precipitate was filtered off and dried, yielding 0.42 g of 4-[4-[[(4-methylphenyl)amino]carbonyl]-1-piperazinyl]-benzoic acid, ethyl ester (interm. 1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. extractionwas then extracted with water
  3. extractionThe organic layer was extracted with a saturated NaCl-solution and again with water
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered off
  7. customthe filtrate was evaporated
  8. stirringThe residue was stirred in DIPE
  9. filtrationthe formed precipitate was filtered off
  10. washwashed with DIPE
  11. customdried
  12. customA part (0.5 g) of the residue (14.3 g, 90%) was crystallized from 2-propanol (10 ml)
  13. filtrationthe formed precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-6fa89c549ef74665a64b70e2202ff80b
Source dataset
uspto-grants-2009_03
Patent number
US07501417B2

Reaction notes

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