Benzoyl chloride → Benzamide, N-(4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)-, monohydrochloride

HRID 1031874Notes

Reaction equation

HRID 1031874 reaction equation
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:17][C:18]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:21]=[C:20]([CH2:30][CH2:31][CH3:32])[N:19]=1>ClC(Cl)C>[ClH:9].[O:27]1[CH2:26][CH2:25][N:24]([C:22]2[N:21]=[C:20]([CH2:30][CH2:31][CH3:32])[N:19]=[C:18]([NH:17][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:23]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 3080166HCID 3080166, compound

Product 1

HCID 3080136Benzamide, N-(4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)-, monohydrochlorideYield 66.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent3×

Procedure

A solution of 7.7 g (0.055 mole) of benzoyl chloride in 50 ml of dichloroethane and a solution of 5.5 g (0.055 mole) of triethylamine in ml of dichloroethane are successively added into a solution of 11.2 g (0.05 mole) of 2-amino-4-morpholino-6-propyl-1,3,5-triazine in 200 ml of dichloroethane at room temperature. The mixture is heated under reflux for 6 hours and cooled to room temperature. It is washed successively with water, with an aqueous solution of sodium bicarbonate and then with water once again. The organic phase is dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue obtained is chromatographed on silica (eluent: 95:5 (v/v) dichloromethane-ethanol) and finally recrystallized from a 50:50 mixture (v/v) of diethyl etherhexane. The product forms a hydrochloride in the diethyl ether. 12.1 g of N-(4-morpholino-6-propyl-1,3,5-triazin-2-yl)-benzamide hydrochloride are thus obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 6 hours
  3. washIt is washed successively with water, with an aqueous solution of sodium bicarbonate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue obtained
  7. customis chromatographed on silica (eluent: 95:5 (v/v) dichloromethane-ethanol)
  8. customfinally recrystallized from a 50:50 mixture (v/v) of diethyl etherhexane

Sources & evidence

ORD record
ord-0a56f50a8eae434a9a462771b0b20cac
Source dataset
uspto-grants-1990_09
Patent number
US04956367

Reaction notes

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