Dimethylamine, hydrochloride → HCID 20066633, compound

HRID 358765Notes

Reaction equation

HRID 358765 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:10][CH:9]1[C:28]([OH:30])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:32]1[C:36](=O)CC[C:33]1=O.C1(N=C=NC2CCCCC2)CCCCC1.Cl.CNC>O1CCOCC1.C(N(CC)CC)C>[CH3:33][N:32]([CH3:36])[C:28]([CH:9]1[CH2:10][N:11]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[O:30]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 20066641HCID 20066641, compound

Product 1

HCID 20066633HCID 20066633, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of 1-tert-butoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylic acid (3.0 g), N-hydroxysuccinimide (1.2 g) and dioxane (30 ml) is added, at room temperature, dicyclohexyl carbodiimide (2.6 g). The mixture is stirred for 5 hours. To a mixture of dimethylamine hydrochloride (8.0 g), triethylamine (10.0g) and dioxane (30 ml) is added dropwise at 0° C the solution of active ester prepared above. The reaction mixture is concentrated, and the concentrate is dissolved in dichloromethane. The solution is washed with a 5% aqueous solution of citric acid and a saturated aqueous solution of sodium hydrogencarbonate, which is then dried and further concentrated. The crude product is subjected to a silica gel column chromatography (ethyl acetate-methanol=9:1) to afford N,N-dimethyl 1-tert-butoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2carboxamide (2.1 g) as colorless crystals, m.p. 146-147° C.

Workup

  1. additionis added, at room temperature
  2. customprepared above
  3. concentrationThe reaction mixture is concentrated
  4. dissolutionthe concentrate is dissolved in dichloromethane
  5. washThe solution is washed with a 5% aqueous solution of citric acid
  6. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, which is then dried
  7. concentrationfurther concentrated

Sources & evidence

ORD record
ord-bb48b29ddd65476dbec378c1d349c8c8
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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