Phentermine → N-(alpha,alpha-Dimethylphenethyl)-2-quinoxalinecarboxamide

HRID 2302047Notes

Reaction equation

HRID 2302047 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[CH3:14][C:15]([NH2:24])([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:16]>ClCCl.C(OCC)(=O)C>[CH3:16][C:15]([NH:24][C:11]([C:2]1[CH:3]=[N:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)=[O:12])([CH3:14])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 4771PhentermineHCID 2734681Quinoxaline-2-carbonyl chloride

Product 1

HCID 9948445N-(alpha,alpha-Dimethylphenethyl)-2-quinoxalinecarboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-Quinoxaloyl chloride (207 mg, 1.07 mmol) in dichloromethane (1 mL) was added to a solution of phentermine (160 mg, 1.07 mmol) in dichloromethane (3 mL) cooled to 0° C.The reaction was allowed to warm to 25° C.After 5 min, the reaction mixture was diluted with ethyl acetate (40 mL) and washed with 1 M sodium hydroxide (2×40 mL). The organic layer was dried (anhydrous magnesium sulfate), filtered through silica gel, and rotary evaporated. This provided 51 mg (16%) of (108):

Workup

  1. temperatureto warm to 25° C
  2. washwashed with 1 M sodium hydroxide (2×40 mL)
  3. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  4. filtrationfiltered through silica gel, and rotary evaporated

Sources & evidence

ORD record
ord-90e2dffe2b674fac9633a9c9c7f55a5a
Source dataset
uspto-grants-2002_08
Patent number
US06429207B1

Reaction notes

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