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

HRID 907495Notes

Reaction equation

HRID 907495 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].[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:21]

Participants

6

Reactant 3

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

Product 2

HCID 594074642-Methyl-1-phenyl-2-(pyridin-2-yl)propan-1-oneHCID 59407467(S)-2-methyl-1-phenyl-2-(pyridine-2-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(S)-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 4 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-17b23bd2947844a18f5181c0f693c2c3
Source dataset
uspto-grants-2011_09
Patent number
US08013165B2

Reaction notes

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