Sodium hydride → 3-[3-(4-Morpholinylmethyl)phenoxy]1-propanamine

HRID 1981351Notes

Reaction equation

[H-].[Na+].[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)[CH2:5][CH2:4]1.Cl.Cl[CH2:19][CH2:20][CH2:21][NH2:22]>CN(C)C=O>[O:3]1[CH2:4][CH2:5][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[O:16][CH2:19][CH2:20][CH2:21][NH2:22])[CH2:7][CH2:8]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a 80% suspension of 0.28 mol of sodium hydride in dimethylformamide, 0.06 mol of 3-morpholinomethylphenol is added portionwise, under stirring at a temperature of about 20° C., then the mixture is stirred 15 minutes at room temperature and a solution of 0.08 mol of 3-chloropropylamine hydrochloride in 20 ml of dimethylformamide is added thereto at 5°-10° C. The reaction mixture is stirred 24 hours at room temperature, then, after addition of 400 ml of ice-water, it is extracted 4 times with 100 ml of ethyl acetate. The organic solution is washed twice with 30 ml of 10% sodium hydroxide, then 3 times with 20 ml of water. The mixture is dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. Thus, 3-(3-morpholinomethylphenoxy)propylamine is obtained, in the form of a yellow oil. Yield: 64%.

Workup

stirringthe mixture is stirred 15 minutes at room temperature
customat 5°-10° C
stirringThe reaction mixture is stirred 24 hours at room temperature
extractionis extracted 4 times with 100 ml of ethyl acetate
washThe organic solution is washed twice with 30 ml of 10% sodium hydroxide
dry with materialThe mixture is dried over anhydrous sodium sulfate
customevaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-0da7cd047215405ab67d738f242ce355
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04514408

Reaction notes

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