Hydrochloric Acid → 1-Phenyl-2-(pyridin-2-yl)propan-1-one

HRID 907490Notes

Reaction equation

HRID 907490 reaction equation
[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:11])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:4].Cl.C(OC(C)C)(=[O:21])C>C(O)(C)C>[CH3:11][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:1])[C@@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:4].[C:5]1([C:3](=[O:21])[CH:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH3:1])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7915Isopropyl AcetateHCID 468296142-Methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine

Product 2

HCID 115502561-Phenyl-2-(pyridin-2-yl)propan-1-oneHCID 46829615(r)-2-Methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(R)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine is prepared starting from racemic 2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine using chiral SFC chromatography. This oil is dissolved in isopropyl acetate and a solution of 5-6 N HCl in isopropyl alcohol is added. The mixture is concentrated, and triturated in ether to yield 3 as a white solid. M.p.=188° C. 1HNMR (300 MHz, CD3OD): δ 1.59 (s, 3H), 1.76 (s, 3H), 5.09 (s, 1H), 7.25-7.28 (m, 2H), 7.38-7.40 (m, 3H), 8.00 (t, J=6.6 Hz, 1H), 8.11 (d, J=6.9 Hz, 1H), 8.56 (t, J=7.8 Hz, 1H), 8.77 (d, J=5.7 Hz, 1H). MS: m/z 227.

Workup

  1. concentrationThe mixture is concentrated
  2. customtriturated in ether

Sources & evidence

ORD record
ord-e67d01ea5ec34a18b2fe53a92bac8501
Source dataset
uspto-grants-2011_09
Patent number
US08013165B2

Reaction notes

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