Reaction #4605

Reaction equation

5,6,7,8-Tetrahydroquinoline

sodamide

3-Chloropropylamine hydrochloride

→

3-(5,6,7,8-tetrahydroquinol-8-yl)propylamine

Yield 26.5%

Solvents

ammonia

Conditions

Workup

1. 1
   Otherto give a dark red coloured solution
2. 2
   Otherquenched with ammonium chloride (20 g)
3. 3
   Otherto evaporate
4. 4
   Otherthe residues were partitioned between chloroform and water
5. 5
   Extractionextracted with chloroform
6. 6
   Dryingthe chloroform extracts were dried
7. 7
   Otherevaporated
8. 8
   workup.DISTILLATIONdistilled

Procedure

5,6,7,8-Tetrahydroquinoline (20 g) was added quickly to sodamide (17.6 g) in liquid ammonia (250 ml) to give a dark red coloured solution. 3-Chloropropylamine hydrochloride (28.9 g) was added in portions over four hours when loss of colour was permanent after which the reaction was stirred for a further 2 hours and then quenched with ammonium chloride (20 g). The liquid ammonia was allowed to evaporate and the residues were partitioned between chloroform and water. The pH was lowered to 6 and the chloroform layer was discarded. The aqueous layer was basified (pH 12-14), and extracted with chloroform, the chloroform extracts were dried, combined, evaporated and the residue was vacuum distilled to give 3-(5,6,7,8-tetrahydroquinol-8-yl)propylamine (7.58 g), b.p. 92°-94° C. at 0.1 mm Hg.

Source