1-Phenethylamine, (-)- → HCID 13336773, compound

HRID 1462901Notes

Reaction equation

HRID 1462901 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH:12]2[C:21]([OH:23])=[O:22])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[C@H](N)C1C=CC=CC=1>CC(O)C>[C:1]1([CH2:7][O:8][C:9]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][C@H:12]2[C:21]([OH:23])=[O:22])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 13336772HCID 13336772, compound

Product 1

HCID 13336773HCID 13336773, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(±)-1,2,3,4-Tetrahydro-1-phenylmethoxycarbonyl-2-quinolinecarboxylic acid (243 g) was dissolved with warming in 2-propanol (1170 ml) and this solution was treated with (S)(-)-α-methylbenzylamine (100 ml). After stirring overnight, the solid product was filtered and dried to constant weight at 60°; yield 160 g, m.p. 135°-148°, [α]D20 -25.6° (c 1, methanol). This crystalline salt was recrystallized from 2-propanol (1400 ml) and washed with ether (400 ml); yield 108 g, m.p. 155°-159°, [α]D20 -50.0° (c 1, methanol). This product was again recrystallized from 2-propanol (1100 ml) and washed with ether (500 ml); yield 84 g, m.p. 159°-160°, [α]D20 -54.9° (c 1, methanol). This salt was added to a mixture of ethyl acetate (500 ml) and 5% aqueous potassium hydrogen sulfate (1000 ml) and stirred for one hour. The layers were separated and the aqueous layer extracted with additional ethyl acetate (250 ml). The organic phase and extract were combined and washed with water (500 ml), dried over magnesium sulfate and activated charcoal, and concentrated to an oily residue which rapidly crystallized to yield (S)(-)-1,2,3,4-tetrahydro-1-phenylmethoxycarbonyl-2-quinolinecarboxylic acid, 57 g, m.p. 75°-79°, [α]D20-82.9° (c 1, methanol). This product was dissolved in methanol (400 ml) and hydrogenated over 5% Pd on carbon (2.0 g) at 40 psi for three hours. The catalyst was filtered and the filtrate concentrated under reduced pressure to an oily residue. Addition of concentrated hydrochloric acid (30 ml) to the residue gave (S)(-)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid hydrochloride; yield 23.6 g, m.p. 172°-176°, [α]D20 -17° (c 1, 0.5 N HCl).

Workup

  1. filtrationthe solid product was filtered
  2. customdried to constant weight at 60°
  3. customThis crystalline salt was recrystallized from 2-propanol (1400 ml)
  4. washwashed with ether (400 ml)
  5. customThis product was again recrystallized from 2-propanol (1100 ml)
  6. washwashed with ether (500 ml)
  7. additionThis salt was added to a mixture of ethyl acetate (500 ml) and 5% aqueous potassium hydrogen sulfate (1000 ml)
  8. stirringstirred for one hour
  9. customThe layers were separated
  10. extractionthe aqueous layer extracted with additional ethyl acetate (250 ml)
  11. extractionThe organic phase and extract
  12. washwashed with water (500 ml)
  13. dry with materialdried over magnesium sulfate and activated charcoal
  14. concentrationconcentrated to an oily residue which
  15. customrapidly crystallized

Sources & evidence

ORD record
ord-6d624cda22aa4b2192e3d8d3d43b6e73
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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