1-Phenethylamine, (+)- → HCID 60123694, compound

HRID 271822Notes

Reaction equation

HRID 271822 reaction equation
[N:1]1[C:10]2[C:9](=O)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:12][C@@H:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO.C[C@@H](N)C1C=CC=CC=1>[N:1]1[C:10]2[C:9](=[N:20][C@@H:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:12])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 117447776,7-Dihydro-5H-quinoline-8-one

Product 1

HCID 60123694HCID 60123694, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 6431891-Phenethylamine, (+)-CatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 6,7-dihydro-5H-quinolin-8-one (3.02 g, 20.5 mmol) in dry MeOH (100 mL) was added (R)-(+)-α-methylbenzylamine (2.61 mL, 20.5 mmol) via syringe. The resulting mixture was stirred 24 h, at which point additional (R)-(+)-α-methylbenzylamine (0.26 mL, 2.0 mmol) was added and the reaction was stirred for an additional 24 h. The solvent was removed in vacuo and dried for 3 days at room temperature under reduced pressure (0.1 Torr) to afford 5.38 g (95%) of the title compound as a red/brown solid. [α]D=−126.0 (c 1.04, CHCl3); 1H NMR (CDCl3) δ 1.55 (d, 3H, J=6.9 Hz), 2.17-2.29 (m, 2H), 7.35 (t, 2H, J=7.8 Hz), 4.39 (q, 1H, J=6.6 Hz), 4.72 (t, 1H, J=4.7 Hz), 5.50 (br s, 1H), 7.07 (dd, 1H, J=7.5, 5.1 Hz) 7.20-7.47 (m, 6H), 8.37 (d, 1H, J=2.4 Hz); 13C NMR (CDCl3) δ 21.99, 25.68, 28.29, 53.79, 98.12, 122.43, 126.33, 127.03, 128.92, 132.63, 135.09, 139.47, 146.36, 150.48. ES-MS m/z 251 (M+H).

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customdried for 3 days at room temperature under reduced pressure (0.1 Torr)

Sources & evidence

ORD record
ord-a4339b5699924a29ade8968add445e3e
Source dataset
uspto-grants-2008_11
Patent number
US07452994B2

Reaction notes

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