N-(3-Aminopropyl)morpholine → HCID 90102454, compound

HRID 1052450Notes

Reaction equation

HRID 1052450 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[O:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][NH2:21])[CH2:14][CH2:13]1>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([NH:21][CH2:20][CH2:19][CH2:18][N:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chloride

Product 1

HCID 90102454HCID 90102454, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4,6-Dichloropyrimidine-5-carbonyl chloride (600 mg, 2.84 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dissolved in dichloromethane (10 ml) and TEA (395 μl, 2.83 mmol) was added. To this solution, 3-morpholinopropan-1-amine (410 mg, 2.84 mmol) was added dropwise and the mixture was stirred for 30 min. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. The crude (1.13 g, 87% purity, 100% yield) was used in the next synthetic step without further purification.

Workup

  1. washwashed with 4% sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude (1.13 g, 87% purity, 100% yield) was used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-ca1093c6124046f88d75670578d53674
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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