Triethylamine → HCID 16074372, compound

HRID 1860450Notes

Reaction equation

HRID 1860450 reaction equation
Cl.Cl.[CH2:3]([N:5]([C:8]([O:10][CH2:11][CH:12]1[CH2:17][NH:16][CH2:15][CH2:14][NH:13]1)=[O:9])[CH2:6][CH3:7])[CH3:4].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31]>C(Cl)Cl.C(Cl)Cl.CO.[NH4+].[OH-]>[CH3:39][O:38][C:34]1[CH:33]=[C:29]([CH:28]=[C:27]([O:26][CH3:25])[C:35]=1[O:36][CH3:37])[C:30]([N:16]1[CH2:15][CH2:14][NH:13][CH:12]([CH2:11][O:10][C:8]([N:5]([CH2:6][CH3:7])[CH2:3][CH3:4])=[O:9])[CH2:17]1)=[O:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 70030950HCID 70030950, compound

Product 1

HCID 16074372HCID 16074372, compoundYield 53.33%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21896990Dichloromethane methanol ammonium hydroxideSolvent

Procedure

19.86 g (86 mmol) of 2-(N,N-diethylaminocarbonyloxymethyl)piperazine dihydrochloride prepared in accordance with step 2.2 of Example 2 are dissolved in 400 ml of CH2Cl2 and 42 ml (3.5 equivalents) of triethylamine in a 1 liter ground-necked conical flask on which is fitted an addition funnel, and which is immersed in an ice bath. A solution containing 19.83 g (86 mmol) of 3,4,5-trimethoxybenzoyl chloride in 200 ml of CH2Cl2 is added dropwise to the solution thus obtained. The reaction is monitored by thin-layer chromatography, using a CH2Cl2/MeOH/NH4OH mixture (80/20/0.5 v/v/v) as eluent, until the starting amine has disappeared. The solution is then washed with saturated NaHCO3 solution and then with water until a neutral pH is obtained. The organic phase is then dried (MgSO4), filtered and evaporated and the residue obtained is chromatographed on a column of silica gel with an MeOH/CH2Cl2 mixture (1/99 v/v) as eluent. 18.75 g of 4-(3′,4′,5′-trimethoxybenzoyl)-2-(N,N-diethylaminocarbonyloxymethyl)piperazine are thus obtained in the form of a viscous oil. Yield: 53.33%.

Workup

  1. customwhich is immersed in an ice bath
  2. additionis added dropwise to the solution
  3. customthus obtained
  4. washThe solution is then washed with saturated NaHCO3 solution
  5. customwith water until a neutral pH is obtained
  6. dry with materialThe organic phase is then dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue obtained
  10. customis chromatographed on a column of silica gel with an MeOH/CH2Cl2 mixture (1/99 v/v) as eluent

Sources & evidence

ORD record
ord-052497d24b5e40e3aa381cedd2832394
Source dataset
uspto-grants-2003_03
Patent number
US06531476B1

Reaction notes

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