Hydrochloric Acid → 1-[4-(Quinolin-2-yl-methoxy)phenyl]-1-pentylamine
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH2:23][CH2:24][CH2:25][CH3:26])C(O)=O)=[CH:15][CH:14]=1.C1(OP(=O)(O)OC2C=CC=CC=2)C=CC=CC=1.[N-:44]=[N+]=[N-].C(N(CC)CC)C.Cl.[OH-].[Na+]>CN(C)C=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([NH2:44])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
10.5 g (30 mmol) of 2-[4-(quinolin-2-yl-methoxy)phenyl]-caproic acid and 7.7 ml (36 mmol) of phosphoric acid diphenylester-azide are dissolved in 100 ml of dimethylformamide at 0° C. and 10 ml (72 mmol) of triethylamine are added. The mixture is heated at 70° C. for 1 hour and cooled to 0° C., 75 ml of 5 normal hydrochloric acid are added dropwise and the mixture is again heated at 70° C. for 1 hour. The reaction mixture is poured onto water, rendered alkaline with 2-normal sodium hydroxide solution and extracted 5 times with ethyl acetate. After drying over Na2SO4, the extract is evaporated. The product crystallizes out.
Workup
- temperaturecooled to 0° C.
- temperaturethe mixture is again heated at 70° C. for 1 hour
- additionThe reaction mixture is poured onto water
- extractionextracted 5 times with ethyl acetate
- dry with materialAfter drying over Na2SO4
- customthe extract is evaporated
- customThe product crystallizes out
Sources & evidence
- ORD record
- ord-83e0e5c69ed741ecb3e7ffc32684ded2
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05179106
Reaction notes
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