Diisopropylamine → HCID 20097372, compound

HRID 1769804Notes

Reaction equation

HRID 1769804 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[CH:19](=[N:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:20].[CH3:26][O:27][C:28]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[C:29]=1[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>CCOCC.O.C1COCC1>[CH3:43][O:42][C:38]1[CH:39]=[CH:40][CH:41]=[C:28]([O:27][CH3:26])[C:29]=1[C:30]([OH:31])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:20][CH:19]=[N:21][C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 8058HexaneHCID 138901N-Ethylidene-2-methylpropan-2-amineHCID 872417Methanone, (2,6-dimethoxyphenyl)phenyl-HCID 178418339Butyllithium

Product 1

HCID 20097372HCID 20097372, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of diisopropylamine (10.1 g, 0.1 mol) in dry ether (100 ml) was cooled to -10°. A solution of butyl lithium in hexane (65 ml, 0.1 mol) was added, and the mixture was stirred at -10° for 20 min. A solution of N-ethylidene-tert.butylamine (10 g, 0.1 mol) in dry ether (100 ml) was added and the solution was stirred at 0° for 20 min. After cooling to -30° a solution of 2,6-dimethoxybenzophenone (24.1 g, 0.1 mol) in dry ether (100 ml), containing 30 ml THF, was added. The mixture was then stirred at ambient temperature for 20 h and hydrolized with water. The organic phase was washed with water, dried and evaporated, giving 32 g (94%) of N-(3-(2,6-dimethoxyphenyl)-3-hydroxy-3phenylpropylidene)tert.butylamine as an oil.

Workup

  1. stirringthe solution was stirred at 0° for 20 min
  2. additionwas added
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-be896e615eaf408c97a14da6c7d37bc6
Source dataset
uspto-grants-1995_01
Patent number
US05382600

Reaction notes

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