Acetyl chloride → Ethanol, 2-((4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)amino)-, acetate (ester)

HRID 1031875Notes

Reaction equation

HRID 1031875 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[O:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:23]=[C:22]([CH2:24][CH2:25][CH3:26])[N:21]=[C:20]([NH:27][CH2:28][CH2:29][OH:30])[N:19]=2)[CH2:14][CH2:13]1>ClCCl>[C:1]([O:30][CH2:29][CH2:28][NH:27][C:20]1[N:19]=[C:18]([N:15]2[CH2:14][CH2:13][O:12][CH2:17][CH2:16]2)[N:23]=[C:22]([CH2:24][CH2:25][CH3:26])[N:21]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471Triethylamine2×HCID 1309282-(4-Morpholino-6-propyl-1,3,5-triazin-2-yl)aminoethanol2×

Product 1

HCID 3080158Ethanol, 2-((4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)amino)-, acetate (ester)Yield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
5 °C

Procedure

4 3 g (0.055 mole) of acetyl chloride, dissolved in 50 ml of dichloromethane, and 5.5 g (0.055 mole) of triethylamine, dissolved in 50 ml of dichloromethane, are simultaneously introduced, between 0° and 5° C., into a solution of 13.4 g (0.05 mole) of 2-[(4-morpholino-6-propyl-1,3,5-triazin-2-yl)amino]-ethanol (compound 1 prepared in Example 1) in 200 ml of dichloromethane. The addition of these two reagents is regulated in a manner such that the acid chloride is always present in the reaction mixture in excess with respect to the triethylamine. The mixture is stirred for one hour at 5° C. and then for 12 hours at room temperature. The reaction mixture is washed successively with an aqueous solution of sodium bicarbonate and with water. It is dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue crystallizes in a mixture of toluene-hexane 1:2. The product obtained is first purified by chromatography on silica (eluent: 95:5 (v/v) dichloromethane-ethanol) and is then firstly recrystallized from a mixture of toluene-hexane 1:1. 9.3 g of 2-[[2-(acetoxy)ethyl]amino]-4-morpholino-6-propyl-1,3,5-triazine are obtained.

Workup

  1. additionThe addition of these two reagents
  2. waitfor 12 hours at room temperature
  3. washThe reaction mixture is washed successively with an aqueous solution of sodium bicarbonate and with water
  4. dry with materialIt is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue crystallizes in a mixture of toluene-hexane 1:2
  7. customThe product obtained
  8. customis first purified by chromatography on silica (eluent: 95:5 (v/v) dichloromethane-ethanol)
  9. customis then firstly recrystallized from a mixture of toluene-hexane 1:1

Sources & evidence

ORD record
ord-e550ff8276ca4442882c35c78760591e
Source dataset
uspto-grants-1990_09
Patent number
US04956367

Reaction notes

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