Sodium amide → 3-(5,6,7,8-Tetrahydroquinol-8-yl)propylamine

HRID 34920

Reaction equation

HRID 34920 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2-].[Na+].Cl.Cl[CH2:15][CH2:16][CH2:17][NH2:18]>N>[N:1]1[C:10]2[CH:9]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 663355,6,7,8-TetrahydroquinolineHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 198517793-(5,6,7,8-Tetrahydroquinol-8-yl)propylamineYield 26.5%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

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.

Workup

  1. customto give a dark red coloured solution
  2. customquenched with ammonium chloride (20 g)
  3. customto evaporate
  4. customthe residues were partitioned between chloroform and water
  5. extractionextracted with chloroform
  6. dry with materialthe chloroform extracts were dried
  7. customevaporated
  8. distillationdistilled

Sources & evidence

ORD record
ord-477c120a9e8a486db0eedc03694403ae
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Linked notes

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