Hydrochloric Acid → HCID 9991761, compound

HRID 649197Notes

Reaction equation

HRID 649197 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1.[BH3-]C#N.[Na+].Cl>CO.C(O)(=O)C>[C:1]1([CH2:7][CH2:8][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 998PhenylacetaldehydeHCID 694601,2,3,4-TetrahydroquinolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 9991761HCID 9991761, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To phenylacetaldehyde (6.0 g, 0.050 mol), 1,2,3,4-tetrahydroquinoline (13 g, 0.1 mol) and acetic acid (0.5 ml) in methanol (50 ml) was added NaBH3CN (1.18 g). After stirring for 1 hour, the mixture was poured into 800 ml 1N HCl and extracted 3×100 ml ether. The combined organic layers were washed 1×100 ml 1N HCl and 2×100 ml H2O, dried (K2CO3) and concentrated to 100 ml. The concentrate was perfused with excess HCl gas to form an oily hydrochloride salt of title product. The solvent was decanted and the residual washed 2×50 ml ether. The washed salt was distributed between excess 5% K2CO3 and ether, and the organic layer separated, dried (K2CO3) and stripped to yield title product as an oil, 6.5 g.

Workup

  1. extractionextracted 3×100 ml ether
  2. washThe combined organic layers were washed 1×100 ml 1N HCl and 2×100 ml H2O
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated to 100 ml

Sources & evidence

ORD record
ord-4542a66f7abe4029b64a4afa10e13fa6
Source dataset
uspto-grants-1988_04
Patent number
US04738972

Reaction notes

Loading…