Hexane → N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamide

HRID 247747

Reaction equation

HRID 247747 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].[CH2:15]([Li])[CH2:16][CH2:17][CH3:18].[CH3:20][CH2:21][CH2:22]CCC.C(=[CH:33][NH2:34])C1C=CC=CC=1>C1COCC1.CCOCC>[CH3:33][NH:34][CH:15]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:18][CH:17]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 8058HexaneHCID 155076Ethenamine, 2-phenyl-HCID 27340052,2,2'-TrimethylpropionanilideHCID 178418339Butyllithium2×

Product 1

HCID 10968937N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamideYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of N-[(2-methyl)phenyl]-2,2-dimethylpropanamide (95.6 g, 0.5 mol) in THF (500 ml, dried over 4 Å molecular sieves) was cooled to 0° C. and treated with 1.6M n-butyllithium in hexane (630 ml, 1.0 mol). The addition of n-butyllithium was complete after 45 minutes. During the addition, the temperature of the mixture was maintained below 10° C. with external cooling. The resultant dianion solution was aged (about 1-2 hrs) at 0° C. until the homogeneous orange solution became a white heterogeneous slurry. The dianion was then quenched with N-benzylidenemethylamine (63.7 g, 0.6 mol) and aged for 30 minutes at 15°-25° C. The reaction mixture was diluted with ether (200 ml), treated with crushed ice (200 g), and stirred for 15 minutes. The organic phase was separated, washed with saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residual oil was crystallized from hexane (400 ml) at 5° C. to give N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamide (121.2 g, 0.39 mol) in 78% yield. The product had a melting point of 85°-86° C.

Workup

  1. additionDuring the addition
  2. temperaturethe temperature of the mixture was maintained below 10° C. with external cooling
  3. custom(about 1-2 hrs)
  4. customat 0° C.
  5. waitaged for 30 minutes at 15°-25° C
  6. customThe organic phase was separated
  7. washwashed with saturated sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residual oil was crystallized from hexane (400 ml) at 5° C.

Sources & evidence

ORD record
ord-2719aa70f12b4ba4b2d8f113f5f3a760
Source dataset
uspto-grants-1987_11
Patent number
US04709093

Linked notes

Loading…